OA21382A - Fungicidal compounds. - Google Patents

Abstract

Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as a pesticides, especially as fungicides.

Description

Fungicidal Compounds

The présent invention relates to microbiocidal methoxyacrylate dérivatives, e.g., as active ingrédients, which hâve microbiocidal activity, in particular, fungicidal activity. The invention 5 also relates to agrochemical compositions which comprise at least one of the methoxyacrylate dérivatives, to processes of préparation of these compounds and to uses of the methoxyacrylate dérivatives or compositions in agriculture or horticulture for controlling or preventing infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, preferably fungi.

EP 0 212 859 and WO 98/03464 describe the use of methoxyacrylate dérivatives for combating phytopathogenic fungi.

According to the présent invention, there is provided a compound of formula (I)

wherein

R¹ is selected from the group consisting of hydrogen, halogen, methyl and methoxy;

R² is selected from the group consisting of hydrogen, halogen, methyl and methoxy;

R³ is selected from the group consisting of hydrogen, halogen, methyl and methoxy;

R⁴ is Ca-Cîcycloalkyl or Cs-Cjcycloalkenyl, wherein said cycloalkyl or cycloalkenyl is optionally substituted by 1, 2 or 3 R⁵ substituents, which may be the same or different;

R⁵ is selected from the group consisting of halogen, hydroxy, cyano, Ci-Cùalkyl, C2-C4alkenyl, Ci-C4haloalkyl, C2-C4haloalkenyl, cyanoCi-C4alkyl, Cs-Côcycloalkyl, Ca-Côhalocycloalkyl,

C3-C6cycloaIkylCi-C4alkyl-, Ca-CôcycloalkylCi-Côalkenyl-, Ci-C4alkoxy, C3-C4alkenyloxy, C3-C4alkynyloxy, Ci-C4haloalkoxy, C3-C6cycIoalkylCi-C4alkoxy-, Ci-CsalkoxyCi-Csalkoxy-, Ci-CsalkoxyCi-Csalkyl-, (=NOR⁶), (=0), phenoxyCi-Csalkyl-, heteroaryloxyCi-Csalkyl-, phenoxy and heteroaryloxy, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring 5 which comprises 1, 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur, and wherein said phenyl or heteroaryl moieties are optionally substituted by 1,2 or 3 R⁷ substituents, which may be the same or different;

R⁶ is selected from the group consisting of Ci-Cealkyl, C3-C6cycloalkyl, Cs-CecycloalkylCi10 Cialkyl-, C3-Cealkynyl, C3-Côalkenyl and Cs-Côhaloalkenyl;

R⁷ is selected from the group consisting of fluoro, chloro, cyano, hydroxy, methyl, ethyl, methoxy, ethoxy, difluoromethyl, trifluoromethyl, difluoromethoxy and trifluoromethoxy, or an agronomically acceptable sait thereof;

or an N-oxide thereof.

It has been found that the novel compounds of formula (I) hâve, a very advantageous level of 20 biological activity for protecting plants against diseases that are caused by fungi.

According to a second aspect of the invention, there is provided an agrochemical composition comprising a fungicidally effective amount of a compound of formula (I) and an agrochemically-acceptable diluent or carrier. Such an agricultural composition may further 25 comprise at least one additional active ingrédient.

According to a third aspect of the invention, there is provided a method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a fungicidally effective amount of a compound of formula (I), or a composition comprising this 30 compound as active ingrédient, is applied to the plants, to parts thereof or the locus thereof.

According to a fourth aspect of the invention, there is provided the use of a compound of formula (I) as a fungicide. According to this particular aspect of the invention, the use may exclude methods for the treatment of the human or animal body by surgery or therapy.

As used herein, the term halogen or “halo” refers to fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo), preferably fluorine, chlorine or bromine.

As used herein, cyano means a -CN group.

As used herein, hydroxy means a -OH group.

As used herein, the term Ci-Côalkyl refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing no unsaturation, having from one 10 to six carbon atoms, and which is attached to the rest of the molécule by a single bond. CiC4alkyl and Ci-Cialkyl are to be construed accordingly. Examples of Ci-Cealkyl include, but are not limited to, methyl, ethyl, n-propyl, 1-methylethyl (iso-propyl), π-butyl, and 1dimethylethyl (7-butyl).

As used herein, the term “cyanoCi-Cealkyl-” refers to a Ci-Cealkyl radical as generally defined above substituted by one or more cyano groups. “cyanoCi-C4alkyl-“is to be construed accordingly.

As used herein, the term Ci-Cealkoxy refers to a radical of the formula -ORa where Ra is a 20 Ci-Côalkyl radical as generally defined above. Ci-C4alkoxy is to be construed accordingly.

Examples of Ci-Côalkoxy include, but are not limited to, methoxy, ethoxy, propoxy, isopropoxy and Z-butoxy.

As used herein, the term Ci-Cehaloalkyl refers to a Ci-Cealkyl radical, as generally defined 25 above, substituted by one or more of the same or different halogen atoms. Ci-C4haloalkyl is to be construed accordingly. Éxamples of Ci-Câhaloalkyl include, but are not limited to chloromethyl, fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl and 2,2,2trifluoroethyl.

As used herein, the term Ci-Cehaloalkoxy refers to a Ci-Cealkoxy group, as defined above, substituted by one or more of the same or different halogen atoms. Ci-C4haloalkoxy is to be construed accordingly. Examples of Ci-Côhaloalkoxy include, but are not limited to, fluorômethoxy, difluoromethoxy, fluoroethoxy, trifluoromethoxy and trifluoroethoxy.

As used herein, the terni “C3-C6cycloalkylCi-C4alkoxy-” refers to a Ci-C4alkoxy radical as generally defined above substituted by one or more Cs-Cécycloalkyl groups as generally defined below.

As used herein, the term C2-C6alkenyl refers to à straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing at least one double bond that can be of either the (E)- or (^-configuration, having from two to six carbon atoms, which is attached to the rest of the molécule by a single bond. C2-C4alkenyl is to be construed accordingly. Examples of C2-Cealkenyl include, but are not limited to, prop-1-enyl, allyl (prop2-enyl) and but-l-enyl.

As used herein, the term C2-C6haloalkenyl refers to a C2-Cealkenyl radical, as generally defined above, substituted by one or more of the same or different halogen atoms.

As used herein, the term C2-C6alkynyl refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one triple bond, having from two to six carbon atoms, and which is attached to the rest of the molécule by a single bond. Examples of C2-Côalkynyl include, but are not limited to, prop-1-ynyl and propargyl (prop-2-ynyl).

As used herein, the term Ci-CaalkoxyCi-Csalkyl- refers to radical of the formula Ra-O-Rbwhere Ra is a C2-C3alkyl radical as generally defined above, and Rb is a Ci-C2alkylene radical as generally defined above.

As used herein, the term Ci-C3alkoxyCi-C3alkoxy- refers to radical of the formula Ra-O-RbO- where Ra is a Ci-Csalkyl radical as generally defined above, and Rb is a Ci-Csalkyl radical as generally defined above.

As used herein, the term C3-C7cycloalkyl refers to a stable, monocyclic ring radical which is fully saturated and contains 3 to 7 carbon atoms. C3-C4cycloalkyl is to be construed accordingly. Examples of Cs-Cycycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

As used herein, the term Cs-Cycycloalkenyl refers to a stable, monocyclic ring radical which is partially unsaturated and contains 3 to 7 carbon atoms. C3-C4cycloalkenyl is to be construed accordingly. Examples of Cs-Cvcycloalkenyl include, but are not limited to, cyclopenten-l-yl, cyclohexen-1 -y 1 and cyclohepten-1 -y 1.

As used herein, the term “C3-C6cycIoalkylCi-C4alkyl-” refers to a Ci-C4alkyl radical as generally defïned above substituted by one or more C3-Côcycloalkyl groups as generally defined above.

As used herein, the term “Cs-CecycloalkylCi-Cealkenyl-” refers to a C2-Cealkenyl radical as generally defined above substituted by one or more Cs-Cecycloalkyl groups as generally defined above.

As used herein, the term “C3-C6cycloalkylC2-C3alkynyl-” refers to a C2-C3alkynyl radical as generally defined above substituted by one or more Cs-Cecycloalkyl groups as generally defined above.

As used herein, the term Cs-Côhalocycloalkyl refers to a Cs-Cecycloalkyl radical, as generally defined above, substituted by one or more of the same or different halogen atoms. C3C4halocycloalkyl is to be construed accordingly.

As used herein, the term “Ci-CealkoxyCs-Cecycloalkyl-” refers to to a Cs-Cecycloalkyl group as defined above substituted by one or more Ci-Cealkoxy groups as generally defined above.

As used herein, the term Ci-C2alkylC3-C6cycloalkyl- refers to to a C3-C6cycloalkyl group as defined above substituted by one or more Ci-C2alkyl groups as defined above.

As used herein, the term “phenoxyCi-C3alkyl-” refers to a phenyl ring attached to a CiCsalkylene radical as generally defined above via an oxygen atom.

As used herein, unless explicitly stated otherwise, the term heteroaryl refers to a 5- or 6membered monocyclic aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur. The heteroaryl radical may be bonded to the rest of the molécule via a carbon atom or heteroatom. Examples of heteroaryl include, furyl, pyrrolyl,

imidazolyl, thienyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl or pyridyl.

As used herein, the terni heteroaryloxyCi-Cjalkyl- refers to a heteroaryl ring as defined above which is attached to a Ci-Cialkylene radical as generally defined above via an oxygen atom.

The presence of one or more possible asymmetric carbon atoms in a compound of formula (I) means that the compounds may occur in chiral isomeric forms, i.e., enantiomeric or diastereomeric forms. Also atropisomers may occur as a resuit of restricted rotation about a single bond. Formula (I) is intended to include ail those possible isomeric forms and mixtures thereof. The présent invention includes ail those possible isomeric forms and mixtures thereof for a compound of formula (I). Likewise, formula (I) is intended to include ail possible tautomers (including lactam-lactim tautomerism and keto-enol tautomerism) where présent. The présent invention includes ail possible tautomeric forms for a compound of formula (I).

In each case, the compounds of formula (I) according to the invention are in free form, in covalently hydrated form, or in sait form, e.g., an agronomically usable or agrochemically acceptable sait form.

The following list provides définitions, including preferred définitions, for substituents R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ with reference to the compounds of formula (I) according to the invention. For any one of these substituents, any of the définitions given below may be combined with any définition of any other substituent given below or elsewhere in this document.

R¹ is selected from the group consisting of hydrogen, halogen, methyl and methoxy. Preferably, R¹ is selected from the group consisting of hydrogen, chloro, fluoro, bromo, methyl and methoxy. More preferably, R¹ is selected from the group consisting of chloro, fluoro, bromo, methyl and methoxy. Even more preferably, R¹ is selected from the group consisting of chloro, bromo and methyl. Most preferably, R¹ is methyl.

R² is selected from the group consisting of hydrogen, halogen, methyl and methoxy. Preferably, R² is selected from the group consisting of hydrogen, fluoro, methyl and methoxy. More preferably, R² is selected from the group consisting of hydrogen, fluoro and methyl. Even more preferably, R² is hydrogen or fluoro. Most preferably, R² is hydrogen.

R³ is selected from the group consisting of hydrogen, halogen, methyl and methoxy. Preferably, R³ is selected from the group consisting of hydrogen, fluoro, methyl and methoxy. More preferably, R³ is selected from the group consisting of hydrogen, fluoro and methyl. Even more preferably, R³ is hydrogen or fluoro. Most preferably, R³ is hydrogen.

R⁴ is Ca-Cîcycloalkyl or Cs-Cycycloalkenyl, wherein said cycloalky or cycloalkenyl is optionally substituted by 1, 2 or 3 R⁵ substituents, which may be the same or different. Preferably, R⁴ is C3-C7cycloalkyl, wherein said cycloalky is optionally substituted by 1, 2 or 3 R⁵ substituents, which may be the same or different. More preferably, R⁴ is C3-C7cycloalkyl optionally substituted by 1 or 2 R⁵ substituents, which may be the same or different. Even more preferably, R⁴ is C3-C7cycloalkyl optionally substituted by 1 R⁵ substituent. Yet even more preferably, R⁴ is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl optionally substituted by 1 R⁵ substituent. Yet even more preferably still, R⁴ is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Further more preferably still, R⁴ is cyclopentyl or cyclohexyl. Most preferably R⁴ is cyclohexyl.

In one embodiment R⁴ is cyclohexyl optionally substituted by 1 R⁵ substituent.

Each R⁵ is independently selected from the group consisting of halogen, hydroxy, cyano, CiC4alkyl, C2-C4alkenyl, Ci-C4haloalkyl, C2-C4haloalkenyl, cyanoCi-C4alkyl, Cs-Cecycloalkyl, Cs-Côhalocycloalkyl, C3-C6cycloalkylCi-C4alkyl-, C3-C6cycloalkylC2-C6alkenyl-, CiC4alkoxy, C3-C4alkenyloxy, C3-C4alkynyloxy, Ci-C4haloalkoxy, C3-CôcycloalkylCi-C4alkoxy, Ci-CsalkoxyCi-Csalkoxy-, Ci-CsalkoxyCi-Csalkyl-, (=NOR⁶), (=0), phenoxyCi-Csalkyl-, heteroaryloxyCi-Csalkyl-, phenoxy and heteroaryloxy, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1,2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur, and wherein said phenyl or heteroaryl moieties are optionally substituted by 1, 2 or 3 R⁷ substituents, which may be the same or different.

Preferably, each R⁵ is independently selected from the group consisting of halogen, hydroxy, cyano, Ci-C4alkyl, C2-C4alkenyl, Ci-C4haloalkyl, C2-C4haloalkenyl, cyanoCi-C4alkyl, C3Cecycloalkyl, Cs-Cehalocycloalkyl, C3-C6cycloalkylCi-C4alkyl-, C3-CôcycloalkylC2Cealkenyl-, Ci-C4alkoxy, C3-C4alkenyloxy, C3-C4alkynyloxy, Ci-C4haloalkoxy, C3C6cycloalkylCi-C4alkoxy-, Ci-CsalkoxyCi-Csalkoxy-, Ci-CsalkoxyCi-Csalkyl-, (=NOR⁶), (=0), phenoxyCi-Caalkyl-, heteroaryloxyCi-Csalkyl-, phenoxy and heteroaryloxy, wherem the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1,2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur, and wherein said phenyl or heteroaryl moieties are optionally substituted by 1 R⁷ substituent.

More preferably, each R⁵ is independently selected from the group consisting of halogen, hydroxy, cyano, Ci-C4alkyl, C2-C4alkenyl, Ci-C4haloalkyl, C2-C4haloalkenyl, cyanoCiC4alkyl, Cs-Cecycloalkyl, Cj-Côhalocycloalkyl, C3-C6cycloalkylCi-C4alkyl-, C3C6cycloaIkylC2-C6alkenyl-, Ci-C4alkoxy, C3-C4alkenyloxy, C3-C4alkynyloxy, CiC4haloalkoxy, C3-C6cycloalkylCi-C4alkoxy-, Ci-CsalkoxyCi-Csalkoxy-, Ci-CsalkoxyCiC₃alkyl-, (=N0R⁶) and (=0).

Even more preferably, each R⁵ is independently selected from the group consisting of halogen, hydroxy, cyano, Ci-C4alkyl, C2-C4alkenyl, Ci-C4haloalkyl, C2-C4haloalkenyl, Cs-Cecycloalkyl, Cs-Côhalocycloalkyl, C3-C6cycloalkylCi-C4alkyl-, C3-C6cycloalkylC2-C6alkenyl-, CiC4alkoxy, Ci-C4haloalkoxy, (=N0R⁶) and (=0).

Even more preferably still, each R⁵ is selected from the group consisting of halogen, Ci-C4alkyl, Ci-C4haloalkyl, C3-Côcycloalkyl, (=N0R⁶) and (=0).

Yet even more preferably still, each R⁵ is selected from the group consisting of fluoro, methyl, trifluoromethyl, cyclopropyl, (=N0CH3) and (=0).

In one embodiment R⁵ is selected from the group consisting of fluoro, hydroxy, cyano, methyl, wo-propyl, difluoromethyl, trifluoromethyl, cyclopropyl, difluoromethoxy, (=N0CH3), (=NOCH₂CH₃) and (=O).

R⁶ is selected from the group consisting of Ci-Côalkyl, C3-C6cycloalkyl, C3-C6cycloalkylCiC2alkyl-, Cs-Cealkynyl, Cs-Cealkenyl and Cs-Côhaloalkenyl. Preferably, R⁶ is selected from the group consisting of Ci-Cealkyl, Cs-Côcycloalkyl, C3-Céalkynyl and C3-CôalkenyL More preferably, R⁶ is Ci-CôalkyL Even more preferably, R⁶ is Ci-Csalkyl, most preferably R⁶ is methyl.

Each R⁷ is independently selected from the group consisting of fluoro, chloro, cyano, hydroxy, methyl, ethyl, methoxy, ethoxy, difluoromethyl, trifluoromethyl, difluoromethoxy and trifluoromethoxy. Preferably, each R⁷ is independently selected from the group consisting of fluoro, chloro, methyl, ethyl, methoxy, ethoxy, difluoromethyl and trifluoromethyl. Even more 5 preferably, each R⁷ is independently selected from the group consisting of fluoro, chloro, methyl and ethyl.

Preferably, in a compound according to formula (I) of the invention;

R¹ is selected from the group consisting of chloro, fluoro, bromo, methyl and methoxy;

R² is hydrogen or fluoro;

R³ is hydrogen or fluoro;

R⁴ is C3-C7cycloalkyl or C3-C?cycloalkenyl, wherein said cycloalkyl or cycloalkenyl is optionally substituted by 1, 2 or 3 R⁵ substituents, which may be the same or different;

each R⁵ is selected from the group consisting of halogen, Ci-C4alkyl, Ci-C4haloalkyl, C315 Côcycloalkyl, (=N0R⁶) and (=0); and

R⁶ is Ci-Csalkyl.

More preferably, in a compound according to formula (I) of the invention;

R¹ is methyl;

R² is hydrogen;

R³ is hydrogen or fluoro;

R⁴ is C3-C7cycloalkyl optionally substituted by 1,2 or 3 R⁵ substituents, which may be the same or different; and each R⁵ is selected from the group consisting of fluoro, methyl, trifluoromethyl, cyclopropyl, 25 (=NOCH₃) and (=0).

Even more preferably, in a compound according to formula (I) of the invention;

R¹ is methyl;

R² is hydrogen;

R³ is hydrogen;

R⁴ is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, wherein said cyclopropyl is optionally substituted by 1 R⁵ substitutent; and

R⁵ is cyclopropyl.

Even more preferably still, in a compound according to formula (I) of the invention;

R¹ is methyl;

R² is hydrogen;

R³ is hydrogen;

R⁴ is cyclopentyl or cyclohexyl.

In one set of embodiments, the compound according to formula (I) is selected from a compound E.l to E.23 or F.l to F.10 listed in tables E and F below.

According to the invention there is also provided an intermediate of formula (Xlb), ^r1\

(Xlb) .

wherein,

R¹ is methyl;

R² is hydrogen;

R³ is hydrogen;

R⁴ is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl (preferably, R⁴ is cyclopentyl or cyclohexyl); and

R¹³ is H or Ci-C4alkyl (preferably, R¹³ is methyl).

In another embodiment of the invention there is also provided an intermediate of formula (XIc),

Ο

. (Xle) wherein,

R¹ is methyl;

R² is hydrogen;

R³ is hydrogen;

R⁴ is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl (preferably, R⁴ is cyclopentyl or cyclohexyl); and

R¹⁴ is H or Ci-C4alkyl (preferably, R¹⁴ is methyl). .

In one embodiment, the compounds of formula (I) according to the invention may be useful for combating phytopathogenic fungi (e.g Alternaria alternata, Phakopsora pachyrhizi, Plasmopara viticola, Sclerotinia sclerotiorum or Septoria tritici also known as Mycosphaerella graminicola) containing a mutation in the mitochondrial cytochrome b conferring résistance to Qo inhibitors (e.g strobilurins such as azoxystrobin, pyraclostrobin, picoxystrobin and trifloxystrobin or fenamidone or famoxadone).

In a further embodiment, the compounds of formula (I) according to the invention may be useful for combating phytopathogenic fungi (e.g Alternaria alternata, Plasmopara viticola, Sclerotinia sclerotiorum or Septoria tritici also known as Mycosphaerella graminicola) containing a mutation in the mitochondrial cytochrome b conferring résistance to Qo inhibitors (e.g strobilurins such as azoxystrobin, pyraclostrobin, picoxystrobin and trifloxystrobin or fenamidone or famoxadone), wherein the mutation is G143A.

In a further embodiment, the compounds of formula (I) according to the invention may be useful for combating phytopathogenic fungi (e.g Phakopsora pachyrhizi) containing a mutation in the mitochondrial cytochrome b conferring résistance to Qo inhibitors (e.g strobilurins such as azoxystrobin, pyraclostrobin, picoxystrobin and trifloxystrobin or fenamidone or famoxadone), wherein the mutation is F129L.

In another embodiment, the invention also relates to a method of controlling or preventing 5 infestation by phytopathogenic fungi in a plant (e.g Alternaria alternate, Plasmopara viticola, Sclerotinia sclerotiorum or Septoria tritici also known as Mycosphaerella graminicola), wherein said phytopathogenic fungi contains a mutation in the mitochondrial cytochrome b conferring résistance to Qo inhibitors (e.g strobliurins such as azoxystrobin, pyraclostrobin, picoxystrobin and trifloxystrobin or fenamidone or famoxadone), said method comprising applying to the plant, to parts thereof or the locus thereof, a fungicidally effective amount of a compound of formula (I). Preferably, a method of controlling or preventing infestation by phytopathogenic fungi (e.g Phakopsora pachyrhizi) in a soybean plant, wherein said phytopathogenic fungi contains a mutation in the mitochondrial cytochrome b conferring résistance to Qo inhibitors (e.g strobliurins such as azoxystrobin, pyraclostrobin, picoxystrobin and trifloxystrobin or fenamidone or famoxadone), said method comprising applying to the plant, to parts thereof or the locus thereof, a fungicidally effective amount of a compound of formula (I). More preferably, a method of controlling or preventing infestation by phytopathogenic fungi (e.g Phakopsora pachyrhizi} in a soybean plant, wherein said phytopathogenic fungi contains a F129L mutation in the mitochondrial cytochrome b conferring résistance to Qo inhibitors (e.g strobliurins such as azoxystrobin, pyraclostrobin, picoxystrobin and trifloxystrobin or fenamidone or famoxadone), said method comprising applying to the plant, to parts thereof or the locus thereof, a fungicidally effective amount of a compound of formula (I).

The level of résistance and therefore the impact on the performance of the fungicide can be measured by the use of a 'Résistance Factor' (RF). The résistance factor can be calculated by dividing the concentration of a fungicide that provides a set level of disease control (i.e. 50 percent) for the 'résistant' fungal strain with the concentration of the same fungicide that provides the same level of disease control for the 'susceptible' strain of the same fungal species (RF = EC50 value of the résistant strain/EC50 value of the sensitive strain). Although there are no set rules, three categories can be defined: 1) RF > 50 = résistant strain, 2) 5 < RF < 50 = less sensitive strain (shift in sensitivity), and 3) RF < 5 = sensitive strain.

In order to obtain résistant fungal strains, a researcher is to locate a host crop and geographical région where the relevant résistance has been reported in the literature or has been observed in agronomie practice. Either leaf samples infected by the target disease or spores, or mycélium of the target disease are then collected from the locations/host crops and sent to a laboratory, where pure cultures would be isolated. The résistant phenotype of the fungal cultures is determined either by conducting a full dose response bioassay and comparing the bioassay 5 results to similar bioassay results for a known susceptible strain of the same species.

Altematively the résistance génotype of the fungal strain can be determined by molecular techniques (e.g. qPCR) if the résistance mechanism for the relevant species is known.

The compounds of formula (I) according to the invention can be made as shown in the following schemes 1 to 16, wherein R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are as defined for a compound of formula 10 (I), unless otherwise stated.

The compounds of formula (II) wherein R¹, R², R³ and R⁴ are as defined above, and R¹⁶ is as defined in Scheme 1, can be obtained via cross coupling transformation between compounds of formula (III), wherein R¹, R² and R³ are as defined for compounds of formula (I), R¹⁶ is as 15 defined in Scheme 1 and R¹¹ is a halide or pseudohalide such as chloro, bromo, iodo, -OSO2CF3 or -OSÛ2(CF2)3CF3, and compounds of formula (IV), wherein R⁴ is as defined for compounds of formula (I) and M is a metalloid species or pseudometalloid species (e.g. M includes but is not limited to MgCl, ZnCl or B(0H)2), optionally in the presence of a métal sait such as LiCl or ZnCh, and a suitable métal catalyst complex, such as chloro(2-dicyclohexylphosphino20 2',4',6'-triisopropyl-l,T-biphenyl)[2-(2'-amino-l,l'-biphenyl)]palladium(II), in an organic solvent such as tetrahydrofuran or 1,4-dioxane at températures between 20°C - 150°C. For related examples, see: Journal of Organic Chemistry, 2010, 75, 6677 - 6680, Journal of the American Chemical Society, 2009,131,7532-7533, European Journal of Médicinal Chemistry, 2018, 147, 238-252, and “Cross-Coupling Reactions: A Practical Guide (Topics in Current 25 Chemistry)”, edited by Norio Miyaura und S. L. Buchwald (éditions Springer), or “MetalCatalyzed Cross-Coupling Reactions”, edited by Armin de Meijere and François Diederich (éditions WILEY-VCH). This is shown in scheme 1.

Altematively compounds of formula (II) can be obtained by reacting compounds of formula 5 (V), wherein R¹, R² and R³ are as defîned for compounds of formula (I), R¹⁶ is as defïned in

Scheme 2 and R¹² is a partially unsaturated, optionally substituted, C3-C?cycloalkenyl, via a réduction method, such as hydrogénation using a hydrogen source in the presence of a catalyst complex such as, palladium on carbon, in an organic solvent such as methanol, tetrahydrofuran or ethyl acetate at températures between 0°C - 150°C. For related examples, see: ACS

Médicinal Chemistry Letters, 2016, 7, 508-51. ‘Handbook of Heterogeneous Catalytic Hydrogénation for Organic Synthesis’ by Shigeo Nishimura (published by Wiley-VCH), or ‘The Handbook of Homogeneous Hydrogénation’ ed. Johannes de Vries and Comelis Elsevier (published by Wiley-VCH). This is shown in scheme 2.

(V)

Scheme 2

Compounds of formula (V), wherein R¹, R² and R³ are as defined for compounds of formula (I), R¹⁶ is as defined in Scheme 3 and R¹² is a partially saturated, and optionally substituted, C3Cîcycloalkenyl, can be obtained via a cross coupling reaction between compounds of formula (III), wherein R¹¹ is a halide or pseudohalide such as chloro, bromo, iodo, -OSO2CF3 or OSO2(CF₂)₃CF3, and compounds of formula (VI), wherein M represents a metalloid or pseudometalloid species (e.g. M includes but is not limited to, Β(ΟΗ)₂, BPin, SnBus) or hydrogen using a suitable catalyst complex, such as palladium(tetrakistriphenylphosphine), in a solvent such as 1,4-dioxane, dimethylformamide or tetrahydrofuran at températures between 0°C - 150°C, and optionally in the presence of a base (e.g. potassium phosphate). For related examples, see: ACS Médicinal Chemistry Letters, 2016, 7, 508-513 and “Cross-Coupling Reactions: A Practical Guide (Topics in Current Chemistry)”, edited by Norio Miyaura and S.L. Buchwald (éditions Springer), or “Metal-Catalyzed Cross-Coupling Reactions”, edited by Armin de Meijere and François Diederich (éditions WILEY-VCH). This is shown in scheme 3.

Scheme 3

Compounds of formula (VII), wherein R¹, R² and R³ are as defined for compounds of formula (I) and R¹¹ is a halide or pseudohalide such as chloro, bromo, iodo, -OSO2CF3 or OSO₂(CF₂)3CF3, can be obtained from compounds of formula (VIII), wherein R¹, R² and R³ are as defined for compounds of formula (I), R¹¹ is as defined above and R¹³ is H or Ci-C4alkyl, via treatment with a suitable base, such as sodium methoxide, and a formylating agent, such as methyl formate, optionally in a suitable solvent (e.g. tetrahydrofuran) to generate compounds of formula (Villa), wherein R¹, R² and R³ are as defined for compounds of formula (I), R¹¹ is as defined above and R^{10 * * * 14 15 * * * * 20} is H or methyl, followed by méthylation with a reagent, such dimethyl sulfate, optionally in the presence of a base such as K2CO3. Alternatively, compounds of formula (VII) can also be obtained directly from compounds of formula (VIII) via treatment with an orthoester, such as HC(0Me)3, optionally in the presence of an acid, such as H2SO4 or

ZnCh, in a suitable solvent (e.g., methanol). For related examples, see: Journal ofAgricultural and Food Chemistry, 2007, 55, 5697-5700, Molécules, 2010, 15, 9024-9034 and Organic Process Research and Development, 2015,19, 639-645. This is shown in scheme 4.

(VIII) (Villa) (Vil)

Scheme 4

Compounds of formula (VIII), wherein R¹, R² and R³ are as defined for compounds of formula (I), R¹¹ is as defined above and R¹³ is H or C1-C4 alkyl, can be obtained from compounds of formula (IX) wherein R¹, R² and R³ are as defined for compounds of formula (I) and R¹¹ is as defined above, by treatment with a base such as K2CO3 and an alkylation agent of formula (X), wherein R¹³ is H or C1-C4 alkyl, in an organic solvent such as dimethylformamide or N-methyl pyrrolidone. Compounds of formula (X) are commercially available or readily prepared from commercially available compounds by standard functional group transformations as described in March ’s Advanced Organic Chemistry, Smith and March, 6^th édition, Wiley, 2007. This is shown in scheme 5. The skilled person would appreciate that compounds of formula (XI) can be prepared in an analogous manner.

Compounds of formula (I) wherein R¹, R², R³ and R⁴ are as defined for compounds of formula 5 (I), can also be obtained from compounds of formula (XI) wherein R¹, R², R³ and R⁴ are as defïned for compounds of formula (I) and R¹³ is H or C1-C4 alkyl, by treatment with a base such as sodium methoxide and a formylating agent such as methyl formate to generate compounds of formula (Xla), wherein R¹, R², R³ and R⁴ are as defïned for compounds of formula (I) and R¹⁴ is H or methyl, followed by méthylation with a reagent such dimethyl sulfate in the presence 10 of a base such as K2CO3. Altematively, compounds of formula (I) can also be obtained directly from compounds of formula (XI) via treatment with an orthoester, such as HC(OMe)3, optionally in the presence of an acid, such as H2SO4 or ZnCh, in a suitable solvent (e.g., methanol). For related examples, see: Journal of Agricultural and Food Chemistry, 2007, 55, 5697-5700, Molécules, 2010,15, 9024-9034 and Organic Process Research and Development, 15 2015,19, 639-645. This is shown in scheme 6.

(XI) (Xla) (1)

Scheme 6

Compounds of formula (XI), wherein R¹, R² and R³ are as defined for compounds of formula (I) and R⁴ is an optionally substituted cyclopropyl group, can be prepared from compounds of formula (XII), wherein R¹, R² and R³ are as defined for compounds of formula (I) and R¹⁵ represents an optionally substituted alkenyl group, by treatment with diiodomethane with an 5 organozinc reagent such as diethyl zinc, optionally in the presence of an acid source, such as trifluoroacetic acid, and in an organic solvent such as dichloromethane. For related examples, see: Organic Reactions, 2001, 58, 1. This is shown in scheme 7.

(XII) (XI)

Scheme 7

Compounds of formula (XII), wherein R¹, R² and R³ are as defined for compounds of formula (I), R¹⁵ is as defined above and R¹³ is H or C1-C4 alkyl, can be obtained from compounds of formula (XIII) wherein R¹, R² and R³ are as defined for compounds of formula (I) and R¹⁵ is as defined above, by treatment with a base such as K2CO3 and an alkylation agent of formula (X), wherein R¹³ is H or C1-C4 alkyl, in an organic solvent such as dimethylformamide or N-methyl pyrrolidone. This is shown in scheme 8. For related examples, see: European Journal of Organic Chemistry, 2015, 2197-2204. Compounds of formula (X) are commercially available or readily prepared from commercially available compounds by standard functional group transformations as described in March ’s Advanced Organic Chemistry, Smith and March, 6^th édition, Wiley, 2007. The skilled person would appreciate that compounds of formula (XI) or formula (VIII) can be prepared in an analogous manner.

Compounds of formula (XIII), wherein R¹, R² and R³ are as defined for compounds of formula (I) and R¹⁵ is as defined above, can be prepared via coupling transformation between compounds of formula (IX), wherein R¹, R² and R³ are as defined for compounds of formula (I) and R¹¹ is a halide or pseudohalide such as chloro, bromo, iodo, -OSO2CF3 or OSO₂(CF₂)3CF3, and compounds of formula (XIV), wherein R¹⁵ is as defined above and M represents a metalloid species or pseudometalloid species (e.g. M includes but is not limited to,

B(OH)₂, BPin, SnBu3) or hydrogen, usng a suitable catalyst complex, such as palladium(tetrakistriphenylphosphine), in a suitable solvent such as dioxane, dimethylformamide or tetrahydrofuran at températures between 0°C - 150°C and optionally a base, such as potassium phosphate or potassium carbonate. For related examples, see: Journal of Médicinal Chemistry, 2015, 58, 9258-9272 and Journal of Médicinal Chemistry, 2014, 57,

1252-1275.This is shown in scheme 9.

(IX) (XIII)

Scheme 9

Compounds of formula (XV), wherein R¹, R² and R³ are as defined for compounds of formula 20 (I), can be prepared via coupling transformation between compounds of formula (XVI) and an optionally substituted Cs-Cycycloalkene in the presence of a suitable acid, (e.g., p-toylsulfonic acid) and in a suitable solvent, such as toluene. For related examples, see: Journal of Organic Chemistry, 1998, 63, 2858. This is shown in scheme 10.

Compounds of formula (XV), can be obtained from a cross coupling reaction between compounds of formula (XVII), wherein R¹¹ is a halide such as chloro, bromo, and iodo, via introduction of a métal, such as lithium or magnésium, and then a R⁴-Hal compound of formula (XVIII) and a suitable catalyst complex, such as iron (III) chloride, in a suitable solvent such as toluene or tetrahydrofuran. For related examples, see: J. Am. Chem. Soc. 2004, 126, 3686. This is shown in scheme 11.

(XVII)

1) Métal

2) R⁴-Hal (XVIII) catalyst

(XV)

Scheme 11

Compounds of formula (XIX), wherein E is nitro, chloro, bromo, formyl, or acyl, can be obtained from an electrophilic aromatic substitution reaction between compounds of formula (XV) and a suitable electrophile. For related examples, see: J. Am. Chem. Soc. 1964, 86, 1067 and^r/v. Synth. Catal. 2010, 352, 3031. This is shown in scheme 12.

(XV) (XIX)

Scheme 12

Altematively, compounds of formula (IX), wherein R¹¹ is halogen, R⁴ or R¹² as defined above, can be prepared from compounds of formula (XX), via nitro group réduction reaction using a

métal (e.g. Pd/C, iron, or Raney Nickel) in a suitable solvent (e.g. MeOH or éthanol) in the presence of a reducing agent (e.g. hydrogen gas, ammonium chloride, formic acid, or hydrazine) at a température between 25°C and 65°C. In some cases, an improved reaction performance is gained when an increase in pressure is applied. For related examples, see: Yoshii, Y. et al Chem.

Commun. (2015), 51, 1070; Takeshiba, H. et al Eur. Pat. Appl., (1997) 807631. Following the nitro group réduction, a radical-nucleophilic aromatic substitution reaction (Sandmeyer) of compounds of formula (XXI) in the presence of a nitrite source (eg, NaNCh or ùo-amylnitrite), and a copper source (eg, CuCN) in an acceptable solvent System, such as aqueous acetonitrile, at suitable températures (e.g. 0°C to 100°C). This reaction is shown in Scheme 13.

Compounds of formula (IX) can be obtained from a Baeyer-Villiger or Dakin oxidation reaction between compounds of formula (XXII), wherein R^Y is H or Me, and a suitable oxidant, such as a peroxyformic acid or hydrogen peroxide. The résultant ester is hydrolyzed to the corresponding phénol. For related examples, see EP2289889. This is shown in scheme 14.

O

(XXII)

1) Baeyer-Villiger oxidation

2) hydrolysis

(IX)

Scheme 14

Altematively, compounds of formula (VIII), wherein R¹¹ is halogen and R¹³ is H or C1-C4 alkyl can be prepared from compounds of formula (XX), via nucleophilic aromatic substitution reactions with compounds of formula (XXIII) in the presence of a nitrite source (eg, NaNCh or zso-amylnitrite) in acidic conditions (eg, H2SO4 or HBF4) and a copper source (eg, CuSO4 or

CuCN) in an acceptable solvent System at suitable températures (e.g. 0°C to 100°C). Such transformations are described in CN 101580477 or Journal of lowa Academy of Science 2010, 116, 27-35 and are shown in the scheme 15. The skilled person would appreciate that compounds of formula (XI) or formula (XII) can be prepared in an analogous manner.

Altematively, compounds of formula (VIII), wherein R¹¹ is halogen and R¹³ is H or C1-C4 alkyl can be prepared from compounds of formula (XXIV), via nucleophilic aromatic substitution 10 reactions with compounds of formula (XXIII) in the presence of a base (eg, CS2CO3), a catalyst (copper source; eg, Cul or CuO), optionally in the presence of a co-reagent (eg, 1,10phenanthroline) in an acceptable solvent System (eg, toluene) at suitable températures (e.g. 0°C to 110°C). Such transformations are described in WO 2007010082 or WO 200837626 and are shown in Scheme 16. The skilled person would appreciate that compounds of formula (XI) or 15 formula (XII) can be prepared in an analogous manner.

Functional group interconversions as described in the previous schemes are known to the persons skilled in the art. Extensive lists of reaction conditions can be found in: Comprehensive Organic Functional Group Transformations, Edited by A. R. Katritzky, O. Meth-Cohn and C. W. Rees. Pergamon Press (Elsevier Science Ltd.), Tarrytown, NY. 1995; or in: Comprehensive

Organic Transformations: A Guide to Functional Group Préparations, Edited by Richard C. Larock, Wiley-VCH, New York 1999.

If the synthesis yields mixtures of isomers, a séparation is generally not necessarily required because in some cases the individual isomers can be interconverted during work-up for use or 10 during application (e. g. under the action of light, acids or bases). Such conversions may also take place after use, e. g. in the treatment of plants in the treated plant, or in the harmful fungus to be controlled.

As already indicated, it has now been found that the novel compounds of formula (I) of the 15 présent invention hâve a very advantageous level of biological activity for protecting plants against diseases that are caused by fungi.

The compounds of formula (I) can be used in the agricultural sector and related fields of use, e.g., as active ingrédients for controlling plant pests or on non-living materials for the control of spoilage microorganisms or organisme potentially harmful to man. The novel compounds 20 are distinguished by excellent activity at low rates of application, by being well tolerated by plants and by being environmentally safe. They hâve very useful curative, préventive and systemic properties and can be used for protecting numerous cultivated plants. The compounds of formula (I) can be used to inhibit or destroy the pests that occur on plants or parts of plants (fruit, blossoms, leaves, stems, tubers, roots) of different crops of useful plants, while at the 25 same time protecting also those parts of the plants that grow later, e.g., from phytopathogenic microorganisms.

The présent invention further relates to a method for controlling or preventing infestation of plants or plant propagation material and/or harvested food crops susceptible to microbial attack by treating plants or plant propagation material and/or harvested food crops wherein an 30 effective amount a compound of formula (I) is applied to the plants, to parts thereof or the locus thereof.

It is also possible to use compounds of formula (I) as fungicide. The term “fungicide” as used herein means a compound that Controls, modifies, or prevents the growth of fungi. The term “fungicidally effective amount” where used means the quantity of such a compound or combination of such compounds that is capable of producing an effect on the growth of fungi. Controlling or modifying effects include ail déviation from natural development, such as killing, retardation and the like, and prévention includes barrier or other défensive formation in or on a plant to prevent fungal infection.

It may also be possible to use compounds of formula (I) as dressing agents for the treatment of plant propagation material, e.g., seed, such as fruits, tubers or grains, or plant cuttings, for the protection against fungal infections as well as against phytopathogenic fungi occurring in the soil. The propagation material can be treated with a composition comprising a compound of formula (I) before planting: seed, for example, can be dressed before being sown. The active compounds of formula (I) can also be applied to grains (coating), either by impregnating the seeds in a liquid formulation or by coating them with a solid formulation. The composition can also be applied to the planting site when the propagation material is being planted, for example, to the seed furrow during sowing. The invention relates also to such methods of treating plant propagation material and to the plant propagation material so treated.

Furthermore, the compounds of formula (I) can be used for controlling fungi in related areas, for example in the protection of technical materials, including wood and wood related technical products, in food storage, in hygiene management.

In addition, the invention could be used to protect non-living materials from fungal attack, e.g. lumber, wall boards and paint.

The compounds of formula (I) are for example, effective against fungi and fungal vectors of disease as well as phytopathogenic bacteria and viruses. These fungi and fungal vectors of disease as well as phytopathogenic bacteria and viruses are for example:

Absidia corymbifera, Altemaria spp, Aphanomyces spp, Ascochyta spp, Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus, Aureobasidium spp. including A. pullulans, Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp. including B. dothidea, B. obtusa, Botrytis spp. inclusing B. cinerea,

Candida spp. including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis, Cephaloascus fragrans, Ceratocystis spp, Cercospora spp. including C. arachidicola, Cercosporidium personatum, Cladosporium spp, Claviceps purpurea, Coccidioides immitis, Cochliobolus spp, Colletotrichum spp. including C. musae, Cryptococcus neoformans, Diaporthe spp, Didymella spp, Drechslera spp, Elsinoe spp,Epidermophyton spp, Erwinia amylovora, Erysiphe spp. including E. cichoracearum, Eutypa lata, Fusarium spp. including F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, F. solani, Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, Helminthosporium spp, Hemileia spp, Histoplasma spp. including H. capsulatum, Laetisaria fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochium nivale, Microsporum spp, Monilinia spp, Mucor spp, Mycosphaerella spp. including M. graminicola, M. pomi, Oncobasidium theobromaeon, Ophiostoma piceae, Paracoccidioides spp, Pénicillium spp. including P. digitatum, P. italicum, Petriellidium spp, Peronosclerospora spp. Including P. maydis, P. philippinensis and P. sorghi, Peronospora spp, Phaeosphaeria nodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp, Phoma spp, Phomopsis viticola, Phytophthora spp. including P. infestans, Plasmopara spp. including P. halstedii, P. viticola, Pleospora spp., Podosphaera spp. including P. leucotricha, Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp, Pseudoperonospora spp. including P. cubensis, P. humuli, Pseudopeziza tracheiphila, Puccinia Spp. including P. hordei, P. recondita, P. striiformis, P. triticina, Pyrenopeziza spp, Pyrenophora spp, Pyricularia spp. including P. oryzae, Pythium spp. including P. ultimum, Ramularia spp, Rhizoctonia spp, Rhizomucor pusillus, Rhizopus arrhizus, Rhynchosporium spp, Scedosporium spp. including S. apiospermum and S. prolificans, Schizothyrium pomi, Sclerotinia spp, Sclerotium spp, Septoria spp, including S. nodorum, S. tritici, Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp, Stagonospora nodorum, Stemphylium spp,. Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilletia spp, Trichoderma spp. including T. harzianum, T. pseudokoningii, T. viride, Trichophyton spp, Typhula spp, Uncinula necator, Urocystis spp, Ustilago spp, Venturia spp. including V. inaequalis, Verticillium spp, and Xanthomonas spp.

The compounds of formula (I) may be used for example on turf, ornamentals, such as flowers, shrubs, broad-leaved trees or evergreens, for example conifers, as well as for tree injection, pest management and the like.

Within the scope of présent invention, target crops and/or useful plants to be protected typically comprise perennial and annual crops, such as berry plants for example blackberries, blueberries, cranberries, raspberries and strawberries; cereals for example barley, maize (corn), millet, oats, rice, rye, sorghum triticale and wheat; fibre plants for example cotton, flax, hemp, jute and sisal; field crops for example sugar and fodder beet, coffee, hops, mustard, oilseed râpe (canola), poppy, sugar cane, sunflower, tea and tobacco; fruit trees for example apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; grasses for example Bermuda grass, bluegrass, bentgrass, ceritipede grass, fescue, ryegrass, St. Augustine grass and Zoysia grass; herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes for example beans, lentils, peas and soya beans; nuts for example almond, cashew, ground nut, hazelnut, peanut, pecan, pistachio and walnut; palms for example oil palm; omamentals for example flowers, shrubs and trees; other trees, for example cacao, coconut, olive and rubber; vegetables for example asparagus, aubergine, broccoli, cabbage, carrot, cucumber, garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and vines for example grapes.

The term useful plants is to be understood as also including useful plants that hâve been rendered tolérant to herbicides like bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors) as a resuit of conventional methods of breeding or genetic engineering. An example of a crop that has been rendered tolérant to imidazolinones, e.g. imazamox, by conventional methods of breeding (mutagenesis) is Clearfield® summer râpe (Canola). Examples of crops that hâve been rendered tolérant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady®, Herculex I® and LibertyLink®.

The term useful plants is to be understood as also including useful plants which hâve been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.

Examples of such plants are: YieldGard® (maize variety that expresses a CrylA(b) toxin); YieldGard Rootworm® (maize variety that expresses a CrylIIB(bl) toxin); YieldGard Plus® (maize variety that expresses a CrylA(b) and a CrylIIB(bl) toxin); Starlink® (maize variety that expresses a Cry9(c) toxin); Herculex I® (maize variety that expresses a CryIF(a2) toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolérance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a CrylA(c) toxin); Bollgard I® (cotton variety that expresses a CrylA(c) toxin); Bollgard II® (cotton variety that expresses a CrylA(c) and a CrylIA(b) toxin); VIPCOT® (cotton variety that expresses a VIP toxin); NewLeaf® (potato variety that expresses a CrylIIA toxin); NatureGard ® Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Btll corn borer (CB) trait), Agrisure® RW (corn rootworm trait) and Protecta®.

The term crops is to be understood as including also crop plants which hâve been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus. ,

Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as δ-endotoxins, e.g. CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Ciy3A, Cry3Bbl or Cry9C, or végétative insecticidal proteins (Vip), e.g. Vipl, Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonising nematodes, for example Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animais, such as scorpion toxins, arachnid toxins, wasp toxins and other insectspecific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins; agglutinins; protéinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosomeinactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroidoxidase, ecdysteroid-UDP-glycosyl-transferase, cholestérol oxidases, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers, such as blockers of sodium or calcium channels, juvénile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases.

Further, in the context of the présent invention there are to be understood by δ-endotoxins, for example CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl or Cry9C, or végétative insecticidal proteins (Vip), for example Vipl, Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinantly by a 5 new combination of different domains of those proteins (see, for example, WO 02/15701).

Truncated toxins, for example a truncated CrylAb, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid replacements, preferably non-naturally présent protease récognition sequences are inserted into the toxin, such as, for example, in. the case of Cry3A055, a cathepsin-G-recognition sequence 10 is inserted into a Cry3A toxin (see WO 03/018810).

Examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0 374 753, WO93/07278, WO95/34656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073.

The processes for the préparation of such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. Cryltype deoxyribonucleic acids and their préparation are known, for example, from WO 95/34656, EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.

The toxin contained in the transgenic plants imparts to the plants tolérance to harmful insects. Such insects can occur in any taxonomie group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera).

Transgenic plants containing one or more genes that code for an insecticidal résistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety that expresses a CrylAb toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bbl toxin); YieldGard Plus® (maize variety that expresses a CrylAb and a Cry3Bbl toxin); Starlink® (maize variety that expresses a Cry9C toxin); Herculex I® (maize variety that expresses a CrylFa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolérance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a CrylAc toxin); Bollgard I® (cotton variety that expresses a CrylAc toxin); Bollgard II® (cotton variety that expresses a CrylAc and a Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A and a CrylAb toxin); NewLeaf® (potato variety that expresses a Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Btll corn borer (CB) trait) and Protecta®.

Further examples of such transgenic crops are:

1. Btll Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered résistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides} by transgenic expression of a truncated Cryl Ab toxin. Btl 1 maize also transgenically expresses the enzyme PAT to achieve tolérance to the herbicide glufosinate ammonium.

2. Btl76 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered résistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides} by transgenic expression of a CrylAb toxin. Btl76 maize also transgenically expresses the enzyme PAT to achieve tolérance to the herbicide glufosinate ammonium.

3. MIR604 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur,

France, registration number C/FR/96/05/10. Maize which has been rendered insect-resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease récognition sequence. The préparation of such transgenic maize plants is described in WO 03/018810.

4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses a Cry3Bbl toxin and has résistance to certain Coleoptera insects.

5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 30 Brussels, Belgium, registration number C/ES/96/02.

6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C/NL/00/10. Genetically modified maize for the expression of ³⁰ the protein Cry 1F for achieving résistance to certain Lepidoptera insects and of the PAT protein for achieving tolérance to the herbicide glufosinate ammonium.

7. NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, 5 B-1150 Brussels, Belgium, registration number C/GB/02/M3/03. Consists of conventionally bred hybrid maize varieties by Crossing the genetically modifïed varieties NK603 and MON 810. NK603 x MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolérance to the herbicide Roundup® (contains glyphosate), and also a CrylAb toxin obtained from Bacillus thuringiensis subsp. kurstaki 10 which brings about tolérance to certain Lepidoptera, include the European corn borer.

The compounds of formula (I) (including any one of compounds E.l to E.23 or F.l to FTO) or fungicidal compositions according to the présent invention comprising a compound of formula (I) may be used in controlling or preventing phytopathogenic diseases, especially 15 phytopathogenic fungi (such as Phakopsora pachyrhizî) on soy bean plants.

In particular, transgenic soybean plants expressing toxins, for example insecticidal proteins such as delta-endotoxins, e.g. CrylAc (CrylAc Bt protein). Accordingly, this may include transgenic soybean plants comprising event MON87701 (see U.S. PatentNo. 8,049,071 and related applications and patents, as well as WO 2014/170327 Al (eg, see paragraph [008] 20 reference to Intacta RR2 PRO™ soybean)), event MON87751 (US. Patent Application Publication No. 2014/0373191) or event DAS-81419 (U.S. Patent No. 8632978 and related applications and patents).

Other transgenic soybean plants may comprise event SYHT0H2 - HPPD tolérance (U.S. Patent Application Publication No. 2014/0201860 and related applications and patents), event 25 MON89788 -glyphosate tolérance (U.S. Pat. No. 7,632,985 and related applications and patents), event MON87708 - dicamba tolérance (U.S. Patent Application Publication No. US 2011/0067134 and related applications and patents), event DP-356043-5 - glyphosate and ALS tolérance (U.S. Patent Application Publication No. US 2010/0184079 and related applications and patents), event A2704-12 - glufosinate tolérance (U.S. Patent Application Publication No.

US 2008/0320616 and related applications and patents), event DP-305423-1 - ALS tolérance (U.S. Patent Application Publication No. US 2008/0312082 and related applications and patents), event A5547-127 - glufosinate tolérance (U.S. Patent Application Publication No. US 2008/0196127 and related applications and patents), event DAS-40278-9 - tolérance to 2,4dichlorophenoxyacetic acid and aryloxyphenoxypropionate (see WO 2011/022469, WO

2011/022470, WO 2011/022471, and related applications and patents), event 127 - ALS tolérance (WO 2010/080829 and related applications and patents), event GTS 40-3-2 glyphosate tolérance, event DAS-68416-4-2,4-dichlorophenoxyacetic acid and glufosinate tolérance, event FG72 - glyphosate and isoxaflutole tolérance, event BPS-CV127-9 - ALS 5 tolérance and GU262 - glufosinate tolérance or event SYHT04R - HPPD tolérance.

The compounds of formula (I) (including any one of compounds E.l to E.23 or F.l to F. 10) or fungicidal compositions according to the présent invention comprising a compound of formula (I) may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsorapachyrhizi) on soy bean plants. In particular, there 10 are known in the scientific literature certain Elite soybean plant varieties where R-gene stacks, conferring a degree of immunity or résistance to spécifie Phakopsora pachyrhizi, hâve been been introgressed in the plant genome, see for example: ''Fighting Asian Soybean RusF, Langenbach C, et al, Front Plant Science 7(797) 2016).

An elite plant is any plant from an elite line, such that an elite plant is a représentative 15 plant from an elite variety. Non-limiting examples of elite soybean varieties that are commercially available to farmers or soybean breeders include: AG00802, A0868, AG0902, A1923, AG2403, A2824, A3704, A4324, A5404, AG5903, AG6202 AG0934; AG1435; AG2031; AG2035; AG2433; AG2733; AG2933; AG3334; AG3832; AG4135; AG4632; AG4934; AG5831; AG6534; and AG7231 (Asgrow Seeds, Des Moines, lowa, USA);

BPR0144RR, BPR4077NRR and BPR4390NRR (Bio Plant Research, Camp Point, 111., USA); DKB17-51 and DKB37-51 (DeKalb Genetics, DeKalb, I1L, USA); DP 4546 RR, and DP 7870 RR (Delta & Pine Land Company, Lubbock, Tex., USA); JG 03R501, JG 32R606C ADD and JG 55R503C (JGL Inc., Greencastle, Ind., USA); NKS 13-K2 (NK Division of Syngenta Seeds, Golden Valley, Minnesota, USA); 90M01, 91M30, 92M33, 93M11, 94M30, 95M30, 97B52, 25 P008T22R2; P16T17R2; P22T69R; P25T51R; P34T07R2; P35T58R; P39T67R; P47T36R;

P46T21R; and P56T03R2 (Pioneer Hi-Bred International, Johnston, lowa, USA); SG4771NRR and SG5161NRR/STS (Soygenetics, LLC, Lafayette, Ind., USA); S00-K5, S11-L2, S28-Y2, S43-B1, S53-A1, S76-L9, S78-G6, S0009-M2; S007-Y4; S04-D3; S14-A6; S20-T6; S21-M7; S26-P3; S28-N6; S30-V6; S35-C3; S36-Y6; S39-C4; S47-K5; S48-D9; S52-Y2; S58-Z4; S6730 R6; S73-S8; and S78-G6 (Syngenta Seeds, Henderson, Ky., USA); Richer (Northstar Seed Ltd.

Alberta, CA); 14RD62 (Stine Seed Co. la., USA); or Armor 4744 (Armor Seed, LLC, Ar., USA).

Thus, in a further preferred embodiment, the compounds of Formula (I) (including any one of compounds E.l to E.23 or F.l to F. 10), or fungicidal compositions according to the présent invention comprising a compound of formula (I), are used to control Phakopsora pachyrhizi, (including fungicidally-resistant strains thereof, as outlined herein) on Elite soybean plant varieties where R-gene stacks, conferring a degree of immunity or résistance to spécifie Phakopsora pachyrhizi, hâve been been introgressed in the plant genome. Numerous benefits may be expected to ensue from said use, e.g. improved biological activity, an advantageous or broader spectrum of activity (inc. sensitive and résistant strains of Phakopsorapachyrhizi), an increased safety profile, improved crop tolérance, synergistic interactions or potentiating properties, improved onset of action or a longer lasting residual activity, a réduction in the number of applications and/or a réduction in the application rate of the compounds and compositions required for effective control of the phytopathogen (Phakopsora pachyrhizi), thereby enabling bénéficiai resistance-management practices, reduced environmental impact and reduced operator exposure.

Fungicidal-resistant strains of Phakopsorapachyrhizi hâve been reported in the scientific literature, with strains résistant to one or more fungicides from at least each of the following fungicidal mode of action classes being observed: sterol demethylation-inhibitors (DMI), quinone-outside-inhibitors (Qol) and succinate dehydrogenase inhibitors (SDHI). See for example: “Sensitivity of Phakopsora pachyrhizi towards quinone-outside-inhibitors and demethylation-inhibitors, and corresponding résistance mechanisms. ” Schmitz HK et al, Pest ManagSci (2014) 70: 378-388; “First détection of a SDH variant with reduced SDHI sensitivity in Phakopsora pachyrhizi Simôes K et al, J Plant Dis Prot (2018) 125: 21-2; “Compétitive fitness of Phakopsora pachyrhizi isolâtes with mutations in the CYP51 and CYTB genes.” Klosowski AC et al, Phytopathology (ΤΑΡίβ) 106: 1278-1284; “Détection of the Fl 29L mutation in the cytochrome b gene in Phakopsora pachyrhizi. Klosowski AC et al, Pest Manag Sci (2016) 72: 1211-1215.

Thus, in a preferred embodiment, the compounds of Formula (I) (including any one of compounds E.l to E.23 or F.l to F. 10), or fungicidal compositions according to the présent invention comprising a compound of formula (I), are used to control Phakopsora pachyrhizi which are résistant to one or more fungicides from any of the following fungicidal MoA classes: sterol demethylation-inhibitors (DMI), quinone-outside-inhibitors (Qol) and succinate dehydrogenase inhibitors (SDHI).

The term “locus” as used herein means fields in or on which plants are growing, or where seeds of cultivated plants are sown, or where seed will be placed into the soil. It includes soil, seeds, and seedlings, as well as established vegetàtion.

The term “plants” refers to ail physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.

The term “plant propagation material” is understood to dénoté generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and végétative material, 10 such as cuttings or tubers, for example potatoes. There can be mentioned for example seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants. Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants can be protected before transplantation by a total or partial treatment by immersion. Preferably “plant propagation material” is understood to 15 dénoté seeds.

The compounds of formula I may be used in unmodifïed form or, preferably, together with the adjuvants conventionally employed in the art of formulation. To this end they may be conveniently formulated in known manner to emulsifiable concentrâtes, coatable pastes, directly 20 sprayable or dilutable solutions or suspensions, émulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g. in polymeric substances. As with the type of the compositions, the methods of application, such as spraying, atomising, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances. The compositions may also contain further adjuvants such as stabilizers, 25 antifoams, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations for obtaining spécial effects.

Suitable carriers and adjuvants, e.g. for agricultural use, can be solid or liquid and are substances useful in formulation technology, e.g. natural or regenerated minerai substances, 30 solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are for example described in WO 97/33890.

Suspension concentrâtes are aqueous formulations in which finely divided solid particles of the active compound are suspended. Such formulations include anti-settling agents and dispersing agents and may further include a wetting agent to enhance activity as well an anti-foam and a crystal growth inhibitor. In use, these concentrâtes are diluted in water and normally applied as a spray to the area to be treated. The amount of active ingrédient may range from 0.5% to 95% of the concentrate.

Wettable powders are in the form of finely divided particles which disperse readily in water or other liquid carriers. The particles contain the active ingrédient retained in a solid matrix. Typical solid matrices include fuller’s earth, kaolin clays, silicas and other readily wet organic or inorganic solids. Wettable powders normally contain from 5% to 95% of the active ingrédient plus a small amount of wetting, dispersing or emulsifying agent.

Emulsifiable concentrâtes are homogeneous liquid compositions dispersible in water or other liquid and may consist entirely of the active compound with a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isophorone and other non-volatile organic solvents. In use, these concentrâtes are dispersed in water or other liquid and normally applied as a spray to the area to be treated. The amount of active ingrédient may range from 0.5% to 95% of the concentrate.

Water dispersible granules disperse in water or other liquid carriers. The granules contain the active ingrédient retained in a solid matrix. Typical solid matrices include fuller’s earth, kaolin clays, silicas and other readily wet organic or inorganic solids. Granules are formed by extrusion, agglomération or spray-drying, and typically range from 0.5 millimétré to 1 centimètre and preferably 1 to 2 millimétrés in diameter. Water dispersible granules normally contain from 5% to 95% of the active ingrédient, and may also contain a small amount of wetting and/or dispersing agents.

Granular formulations include both extrudates and relatively coarse particles and are usually applied without dilution to the area in which treatment is required. Typical carriers for granular formulations include sand, fuller’s earth, attapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, ground corn cobs, ground peanut hulls, sugars, sodium chloride, sodium sulphate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulphate and other organic or inorganic materials which absorb or which can be coated with the active compound. Granular

formulations normally contain 5% to 25% of active ingrédients which may include surfaceactive agents such as heavy aromatic naphthas, kerosene and other petroleum fractions, or vegetable oils; and/or stickers such as dextrins, glue or synthetic resins.

Dusts are free-flowing admixtures of the active ingrédient with finely divided solids such as talc, clays, flours and other organic and inorganic solids which act as dispersants and carriers.

Microcapsules are typically droplets or granules of the active ingrédient enclosed in an inert porous shell which allows escape of the enclosed material to the surroundings at controlled rates. Encapsulated droplets are typically 1 to 50 microns in diameter. The enclosed liquid typically constitutes 50 to 95% of the weight of the capsule and may include solvent in addition to the active compound. Encapsulated granules are generally porous granules with porous membranes sealing the granule pore openings, retaining the active species in liquid form inside the granule pores. Granules typically range from 1 millimétré to 1 centimètre and preferably 1 to 2 millimétrés in diameter. Granules are formed by extrusion, agglomération or prilling, or are naturally occurring. Examples of such materials are vermiculite, sintered clay, kaolin, attapulgite clay, sawdust and granular carbon. Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyuréthanes and starch xanthates.

Other useful formulations for agrochemical applications include simple solutions of the active ingrédient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene and other organic solvents. Pressurised sprayers, wherein the active ingrédient is dispersed in fïnely-divided form as a resuit of vaporisation of a low boiling dispersant solvent carrier, may also be used.

Suitable agricultural adjuvants and carriers that are useful in formulating the compositions of the invention in the formulation types described above are well known to those skilled in the art.

Liquid carriers that can be employed include, for example, water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acétates, diacetonalcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, Ν,Ν-dimethyl formamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkyl pyrrolidinone, ethyl acetate, 2-ethyl hexanol, ethylene carbonate, 1,1,1 -trichloroethane, 5 2-heptanone, alpha pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol diacetate, glycerol monoacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobomyl acetate, isooctane, isophorone, isopropyl benzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxy-propanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl 10 octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octyl amine acetate, oleic acid, oleylamine, o-xylene, phénol, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffm, minerai oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, 15 éthanol, isopropanol, and higher molecular weight alcohols such . as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, etc., ethylene glycol, propylene glycol, glycérine and N-methyl-2-pyrrolidinone. Water is generally the carrier of choice for the dilution of concentrâtes.

Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, diatomaxeous earth, lime, calcium carbonate, bentonite clay, fuller’s earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour and lignin.

A broad range of surface-active agents are advantageously employed in both said liquid and solid compositions, especially those designed to be diluted with carrier before application. These agents, when used, normally comprise from 0.1% to 15% by weight of the formulation. They can be anionic, cationic, non-ionic or polymeric in character and can be employed as emulsifying agents, wetting agents, suspending agents or for other purposes. Typical surface active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulphate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C.sub. 18 ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-C.sub. 16 ethoxylate; soaps, such as sodium stéarate; alkylnaphthalenesulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quatemary amines, such as lauryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stéarate; block copolymers of ethylene oxide and propylene oxide; and salts of mono and dialkyl phosphate esters.

Other adjuvants commonly utilized in agricultural compositions include crystallisation inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, anti-foaming agents, light-blocking agents, compatibilizing agents, aritifoam agents, sequestering agents, neutralising agents and buffers, corrosion 10 inhibitors, dyes, odorants, spreading agents, pénétration aids, micronutrients, émollients, lubricants and sticking agents.

In addition, further, other biocidally active ingrédients or compositions may be combined with the compositions of the invention and used in the methods of the invention and applied 15 simultaneously or sequentially with the compositions of the invention. When applied simultaneously, these further active ingrédients may be formulated together with the compositions of the invention or mixed in, for example, the spray tank. These further biocidally active ingrédients may be fungicides, herbicides, insecticides, bactéricides, acaricides, nematicides and/or plant growth regulators.

Pesticidal agents are referred to herein using their common name are known, for example, from The Pesticide Manual, 15th Ed., British Crop Protection Council 2009.

In addition, the compositions of the invention may also be applied with one or more 25 systemically acquired résistance inducers (“SAR” inducer). SAR inducers are known and described in, for example, United States Patent No. US 6,919,298 and include, for example, salicylates and the commercial SAR inducer acibenzolar-S-methyl.

The compounds of formula (I) are normally used in the form of agrochemical compositions and 30 can be applied to the crop area or plant to be treated, simultaneously or in succession with further compounds. These further compounds can be e.g. fertilizers or micronutrient donors or other préparations, which influence the growth of plants. They can also be sélective herbicides or non-selective herbicides as well as insecticides, fungicides, bactéricides, nematicides, molluscicides or mixtures of several of these préparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation.

The compounds of formula (I) may be used in the form of (fungicidal) compositions for 5 controlling or protecting against phytopathogenic microorganisms, comprising as active ingrédient at least one compound of formula (I) or of at least one preferred individual compound as defined herein, in free form or in agrochemically usable sait form, and at least one of the above-mentioned adjuvants.

The invention therefore provides a composition, preferably a fungicidal composition, comprising at least one compound formula (I) an agriculturally acceptable carrier and optionally an adjuvant. An agricultural acceptable carrier is for example a carrier that is suitable for agricultural use. Agricultural carriers are well known in the art. Preferably said composition may comprise at least one or more pesticidally-active compounds, for example an additional fungicidal active ingrédient in addition to the compound of formula (I).

The compound of formula (I) may be the sole active ingrédient of a composition or it may be admixed with one or more additional active ingrédients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator where appropriate.

Examples of suitable additional active ingrédients include the following: acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenical fungicides, aryl phenyl ketone fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, 25 botanical fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanilate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiolane fungicides, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine fungicides, organophosphorous fungicides, organotin fungicides, oxathiin fungicides, oxazole 30 fungicides, phenylsulfamide fungicides, polysulfide fungicides, pyrazole fungicides, pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quatemary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxaline fungicides, strobilurin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides, thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides, and zinc fungicides.

Examples of suitable additional active ingrédients also include the following: 3-difluoromethyl5 l-methyl-lH-pyrazole-4-carboxylic acid (9-dichloromethylene-1,2,3,4-tetrahydro-1,4methano-naphthalen-5-yl)-amide , 3-difluoromethyl-l-methyl-lH-pyrazole-4-carboxylic acid methoxy-[l-methyl-2-(2,4,6-trichlorophenyl)-ethyl]-amide , l-methyl-3-difluoromethyl-lHpyrazole-4-carboxylic acid (2-dichloromethylene-3-ethyl-l-methyl-indan-4-yl)-amide (1072957-71-1), l-methyl-3-difluoromethyl-lH-pyrazole-4-carboxylic acid (4'10 methylsulfanyI-biphenyl-2-yl)-amide, 1 -methyl-3-difluoromethyl-4H-pyrazole-4-carboxyIic acid [2-(2,4-dichloro-phenyl)-2-methoxy-l-methyI-ethyl]-amide, (5-Chloro-2,4-dimethylpyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone, (5-Bromo-4-chloro-2-methoxypyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone, 2-{2-[(E)-3-(2,6-Dichlorophenyl)-l-methyl-prop-2-en-(E)-ylideneaminooxymethyl]-phenyl}-2-[(Z)-methoxyimino]-N15 methyl-acetamide, 3-[5-(4-Chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine, (E)-Nmethyl-2- [2- (2, 5-dimethylphenoxymethyl) phenyl]-2-methoxy-iminoacetamide, 4-bromo-2cyano-N, N-dimethyl-6-trifluoromethylbenzimidazole-l-sulphonamide, a- [N-(3-chloro-2, 6xylyl)-2-methoxyacetamido]-y-butyrolactone, 4-chloro-2-cyano-N,N - dimethyI-5-ptolylimidazole-l-sulfonamide, N-allyl-4, 5,-dimethyl-2-trimethylsilylthiophene-320 carboxamide, N- (1-cyano-l, 2-dimethylpropyl)-2- (2, 4-dichlorophenoxy) propionamide, N(2-methoxy-5-pyridyl)-cyclopropane carboxamide, (.+-.)-cis-l-(4-chlorophenyl)-2-(lH-l,2,4triazol-1 -yl)-cycloheptanol, 2-( 1 -fërf-butyl)-1 -(2-chloropheny 1)-3-( 1,2,4-triazol-1 -yl)-propan2-oI, 2',6'-dibromo-2-methyl-4-trifluoromethoxy-4'-trifluoromethyl-l ,3-thiazole- 5carboxanilide, l-imidazolyl-l-(4'-chlorophenoxy)-3,3-dimethylbutan-2-one, methyl (E)-2-[225 [6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]3-methoxyacrylate, methyl (E)-2-[2-[6-(2thioamidophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, methyl (E)-2-[2-[6-(2fluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, methyl (E)-2-[2-[6-(2,6difluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacryla te, methyl (E)-2-[2-[3(pyrimidin-2-yloxy)phenoxy]phenyl]-3-methoxyacrylate, methyl (E)-2-[2-[3-(530 methylpyrimidin-2-yloxy)-phenoxy]phenyl]-3-methoxyacrylate, methyl (E)-2-[2-[3-(phenylsulphonyloxy)phenoxy]phenyl-3-methoxyacrylate, methyl (E)-2-[2-[3-(4nitrophenoxy)phenoxy]phenyl]-3-methoxyacrylate, methyl (E)-2-[2-phenoxyphenyl]-3methoxyacrylate, methyl (E)-2-[2-(3,5-dimethyl-benzoyl)pyrrol-l -yl]-3-methoxyacrylate, methyl (E)-2-[2-(3-methoxyphenoxy)phenyl]-3-methoxyacrylate, methyl (E)-2[2-(2 phenylethen-l-yl)-phenyl]-3-methoxyacrylate, methyl (E)-2-[2-(3,5-dichlorophenoxy)pyridin3-yI]-3-methoxyacrylate, methyl (E)-2-(2-(3-(1,1,2,2-tetrafluoroethoxy)phenoxy)phenyl)-3methoxyacrylate, methyl (E)-2-(2-[3-(alpha-hydroxybenzyl)phenoxy]phenyl)-3methoxyacrylate, methyl (E)-2-(2-(4-phenoxypyridin-2-yloxy)phenyl)-3 -methoxyacrylate, methyl (E)-2-[2-(3-n-propyloxy-phenoxy)phenyl]3-methoxyacrylate, methyl (E)-2-[2-(3isopropyloxyphenoxy)phenyl]-3-methoxyacrylate, methyl (E)-2-[2-[3-(2fluorophenoxy)phenoxy]phenyl]-3-methoxyacrylate, methyl (E)-2-[2-(3ethoxyphenoxy)phenyl]-3-methoxyacrylate, methyl (E)-2-[2-(4-terZ-butyl-pyridin-2yloxy)pheny 1] -3 -methoxyacrylate, methyl (E)-2- [2- [3 -(3 -cyanophenoxy)phenoxy]pheny 1] -3 methoxyacrylate, methoxyacrylate, methoxyacrylate, methoxyacrylate, methyl (E)-2- [2- [(3 -methy l-pyridin-2-y loxymethy l)phenyl] -3 methyl (E)-2-[2-[6-(2-methyI-phenoxy)pyrimidin-4-yloxy]phenyl]-3methyl (E)-2-[2-(5 -bromo-pyridin-2-yloxymethyl)phenyl] -3 methyl (E)-2-[2-(3-(3-iodopyridin-2-yloxy)phenoxy)phenyl]-3methoxyacrylate, methyl (E)-2- [2-[6-(2-chloropyridin-3-yloxy)pyrimidin-4-yloxy]phenyl] -3 methoxyac rylate, methyl (E),(E)-2-[2-(5,6-dimethylpyrazin-2ylmethyloximinomethyl)phenyl]-3-methox yacrylate, methyl (E)-2-{2-[6-(6-methylpyridin-2yloxy)pyrimidin-4-yloxy]phenyl}-3-methoxy-a crylate, methyl (E),(E)-2-{ 2-(3methoxyphenyl)methyloximinomethyl]-phenyl}-3-methoxyacrylate, methyl (E)-2-{2-(6-(2azidophenoxy)-pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate, methyl (E),(E)-2-{2-[6phenylpyrimidin-4-yl)-methyloximinomethyl]phenyl}-3-methox yacrylate, methyl (E),(E)-2{2-[(4-chlorophenyl)-methyloximinomethyl]-phenyl}-3-methoxyacryl ate, methyl (E)-2-{2[6-(2-n-propylphenoxy)-l,3,5-triazin-4-yloxy]phenyl}-3-methoxyacr ylate, methyl (E),(E)-2{2-[(3-nitrophenyl)methyloximinomethyl]phenyl}-3-methoxyacrylate, 3-chloro-7-(2-aza2,7,7-trimethyl-oct-3-en-5-ine), 2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide, 3-iodo2-propinyI alcohol, 4-chlorophenyl-3-iodopropargyl formai, 3-bromo-2,3-diiodo-2-propenyl ethylcarbamate, 2,3,3-triiodoallyl alcohol, 3-bromo-2,3-diiodo-2-propenyI alcohol, 3-iodo-2propinyl n-butylcarbamate, 3-iodo-2-propinyl n-hexylcarbamate, 3-iodo-2-propinyl cyclohexyl-carbamate, 3-iodo-2-propinyl phenylcarbamate; phénol dérivatives, such as tribromophenol, tetrachlorophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophene, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl4-chlorophenol, 5-hydroxy-2(5H)-furanone; 4,5-dichlorodithiazolinone, 4,5benzodithiazolinone, 4,5-trimethylenedithiazolinone, 4,5-dichloro-(3H)-l,2-dithiol-3-one, 3,5dimethyl-tetrahydro-l,3,5-thiadiazine-2-thione, N-(2-p-chlorobenzoyIethyl)-hexaminium chloride, acibenzolar, acypetacs, alanycarb, albendazole, aldimorph, allicin, allyl alcohol, ametoctradin, amisulbrom, amobam, ampropylfos, anilazine, asomate, aureofungin, azaconazole, azafendin, azithiram, azoxystrobin, barium polysulfïde, benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentaluron, benthiavalicarb, benthiazole, benzalkonium chloride, benzamacril, benzamorf, benzohydroxamic acid, benzovindiflupyr, berberine, 5 bethoxazin, biloxazol, binapacryl, biphenyl, bitertanol, bithionol, bixafen, blasticidin-S, boscalid, bromothalonil, bromuconazole, bupirimate, buthiobate, butylamine calcium polysulfïde, captafol, captan, carbamorph, carbendazim, carbendazim chlorhydrate, carboxin, carpropamid, carvone, CGA41396, CGA41397, chinomethionate, chitosan, chlobenthiazone, chloraniformethan, chloranil, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, 10 chlorozolinate, chlozolinate, climbazole, clotrimazole, clozylacon, copper containing compounds such as copper acetate, copper carbonate, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper oxyquinolate, copper silicate, copper sulphate, copper tallate, copper zinc chromate and Bordeaux mixture, cresol, cufraneb, cuprobam, cuprous oxide, cyazofamid, cyclafuramid, cycloheximide, cyflufenamid, cymoxanil, 15 cypendazole, cyproconazole, cyprodinil, dazomet, debacarb, decafentin, dehydroacetic acid, di2-pyridyl disulphide 1, Γ-dioxide, dichlofluanid, diclomezine, dichlone, dicloran, dichlorophen, dichlozoline, diclobutrazol, diclocymet, diethofencarb, difenoconazole, difenzoquat, diflumetorim, O, O-di-iso-propyl-S-benzyl thiophosphate, dimefluazole, dimetachlone, dimetconazole, dimethomorph, dimethirimol, diniconazole, diniconazole-M, 20 dinobuton, dinocap, dinocton, dinopenton, dinosulfon, dinoterbon, diphenylamine, dipyrithione, disulfiram, ditalimfos, dithianon, dithioether, dodecyl dimethyl ammonium chloride, dodemorph, dodicin, dodine, doguadine, drazoxolon, edifenphos, enestroburin, epoxiconazole, etaconazole, etem, ethaboxam, ethirimol, ethoxyquin, ethilicin, ethyl (Z)-Nbenzyl-N ([methyl (methyl-thioethylideneamino- oxycarbonyl) amino] thio)-B-alaninate, 25 etridiazole, famoxadone, fenamidone, fenaminosulf, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan, fenoxanil, fenpiclonil, fenpicoxamid, fenpropidin, fenpropimorph, fenpyrazamine, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, flumorph, flupicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutanil, flutolanil, flutriafol, 30 fluxapyroxad, folpet, formaldéhyde, fosetyl, fuberidazole, furalaxyl, furametpyr, furcarbanil, furconazole, furfural, furmecyclox, furophanate, glyodin, griseofulvin, guazatine, halacrinate, hexa chlorobenzene, hexachlorobutadiene, hexachlorophene, hexaconazole, hexylthiofos, hydrargaphen, hydroxyisoxazole, hymexazole, imazalil, imazalil sulphate, imibenconazole, iminoctadine, iminoctadine triacetate, inezin, iodocarb, ipconazole, ipfentrifluconazole, iprobenfos, iprodione, iprovalicarb, isopropanyl butyl carbamate, isoprothiolane, isopyrazam, isotianil, isovaledione, izopamfos, kasugamycin, kresoxim-methyl, LY186054, LY211795, LY248908, mancozeb, mandipropamid, maneb, mebenil, mecarbinzid, mefenoxam, mefentrifluconazole, mepanipyrim, mepronil, mercuric chloride, mercurous chloride, 5 meptyldinocap, metalaxyl, metalaxyl-M, metam, metazoxolon, metconazole, methasulfocarb, methfuroxam, methyl bromide, methyl iodide, methyl isothiocyanate, metiram, metiram-zinc, metominostrobin, metrafenone, metsulfovax, milneb, moroxydine, myclobutanil, myclozolin, nabam, natamycin, neoasozin, nickel dimethyldithiocarbamate, nitrostyrene, nitrothal-isopropyl, nuarimol, octhilinone, ofurace, organomercury compounds, orysastrobin, osthol, 10 oxadixyl, oxasulfuron, oxathiapiprolin, oxine-copper, oxolinic acid, oxpoconazole, oxycarboxin, paclobutrazol, parinol, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, penthiopyrad, phenamacril, phenazin oxide, phosdiphen, phosetyl-Al, phosphorus acids, phthalide, picoxystrobin, piperalin, polycarbamate, polyoxin D, polyoxrim, polyram, probenazole, prochloraz, procymidone, propamidine, propamocarb, propiconazole, 15 propineb, propionic acid, proquinazid, prothiocarb, prothioconazole, pydiflumetofen, pyràcarbolid, pyraclostrobin, pyrametrostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyridinitril, pyrifenox, pyrimethanil, pyriofenone, pyroquilon, pyroxychlor, pyroxyfur, pyrrolnitrin, quatemary ammonium compounds, quinacetol, quinazamid, quinconazole, quinomethionate, quinoxyfen, quintozene, rabenzazole, santonin, sedaxane, silthiofam, 20 simeconazole, sipconazole, sodium pentachlorophenate, spiroxamine, streptomycin, sulphur, sultropen, tebuconazole, tebfloquin, tecloftalam, tecnazene, tecoram, tetraconazole, thiabendazole, thiadifluor, thicyofen, thifluzamide, 2- (thiocyanomethylthio) benzothiazole, thiophanate-methyl, thioquinox, thiram, tiadinil, timibenconazole, tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol, triazbutil, triazoxide, tricyclazole, 25 tridemorph, trifloxystrobin, triflumazole, triforine, triflumizole, triticonazole, uniconazole, urbacide, validamycin, valifenalate, vapam, vinclozolin, zarilamid, zineb, ziram, and zoxamide.

The compounds of the invention may also be used in combination with anthelmintic agents. Such anthelmintic agents include, compounds selected from the macrocyclic lactone class of 30 compounds such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin dérivatives as described in EP- 357460, EP-444964 and EP-594291. Additional anthelmintic agents include semisynthetic and biosynthetic avermectin/milbemycin dérivatives such as those described in US-5015630, WO9415944 and WO-9522552. Additional anthelmintic agents include the benzimidazoles such as albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, and other members of the class. Additional anthelmintic agents include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel or morantel. Additional anthelmintic agents include flukicides, such as 5 triclabendazole and clorsulon and the cestocides, such as praziquantel and epsiprantel.

The compounds of the invention may be used in combination with dérivatives and analogues of the paraherquamide/marcfortine class of anthelmintic agents, as well as the antiparasitic oxazolines such as those disclosed in US-5478855, US- 4639771 and DE-19520936.

The compounds of the invention may be used in combination with dérivatives and analogues of the general class of dioxomorpholine antiparasitic agents as described in WO 96/15121 and also with anthelmintic active cyclic depsipeptides such as those described in WO 96/11945, WO 93/19053, WO 93/25543, EP 0 626 375, EP 0 382 173, WO 94/19334, EP 0 382 173, and 15 EP 0 503 538.

The compounds of the invention may be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide and the like; neonicotinoids such as imidacloprid and 20 the like.

The compounds of the invention may be used in combination with terpene alkaloids, for example those described in International Patent Application Publication Numbers WO 95/19363 or WO 04/72086, particularly the compounds disclosed therein.

Other examples of such biologically active compounds that the compounds of the invention may be used in combination with include but are not restricted to the following:

Organophosphates: acephate, azamethiphos, azinphos-ethyl, azinphos- methyl, bromophos, 30 bromophos-ethyl, cadusafos, chlorethoxyphos, chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton-S-methyl, demeton-S-methyl sulphone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosthiazate, heptenophos, isazophos, isothioate, isoxathion, malathion, methacriphos, methamidophos, methidathion, methyl- parathion, mevinphos, monocrotophos, naled, omethoate, oxydemetonmethyl, paraoxon, parathion, parathion-methyl, phenthoate, phosalone, phosfolan, phosphocarb, phosmet, phosphamidon, phorate, phoxim, pirimiphos, pirimiphos- methyl, profenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, sulprophos, temephos, terbufos, tebupirimfos, tetrachlorvinphos, thimeton, triazophos, trichlorfon, vamidothion.

Carbamates: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-mcumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, UC-51717. .

Pyrethroids: acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl (E) -(1 R)-cis-2,2dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bifenthrin, beta cyfluthrin, cyfluthrin, a-cypermethrin, beta -cypermethrin, bioallethrin, bioallethrin((S)cyclopentylisomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, ethofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), imiprothrin, cyhalothrin, lambda-cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrins (natural products), resmethrin, tetramethrin, transfluthrin, theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin, tralomethrin, Zeta-cypermethrin.

Arthropod growth regulators: a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexafhimuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, chlorfentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) juvenoids: pyriproxyfen, methoprene (including S-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen.

Other antiparasitics: acequinocyl, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl, bromopropylate, BTG-504, BTG-505, camphechlor, cartap, chlorobenzilate, chlordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine, diacloden, diafenthiuron, DBI-3204, dinactin, dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan, ethiprole, ethofenprox, fenazaquin, flumite, MTI- 800, fenpyroximate, fluacrypyrim, flubenzimine, flubrocythrinate, flufenzine, flufenprox, fluproxyfen, halofenprox, hydramethylnon, IKI-220, kanemite, NC-196, neem guard, nidinorterfuran, nitenpyram, SD-35651, WL-108477, 5 pirydaryl, propargite, protrifenbute, pymethrozine, pyridaben, pyrimidifen, NC-1111, R195,RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, silafluofen, silomadine, spinosad, tebufenpyrad, tetradifon, tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad, triazamate, triethoxyspinosyn, trinactin, verbutin, vertalec, YI-5301.

Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenic bacteria, virus and fungi.

Bactéricides: chlortetracycline, oxytetracycline, streptomycin.

Other biological agents: enrofloxacin, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel, triclabendazole.

Thus, compounds of formula (I) can be used in combination with one or more other active ingeredients to provide various fungicidal mixtures. Spécifie examples of such mixtures include (wherein “I” represents a compound of formula (I)): a compound selected from the group of substances consisting ofpetroleum oils + I, l,l-bis(4-chlorophenyl)-2-ethoxyethanol +1, 2,4-dichlorophenyl benzenesulfonate + I, 2-fluoro-N-methyl-N-l-naphthylacetamide + I, 25 4-chlorophenyl phenyl sulfone + I, acetoprole +1, aldoxycarb +1, amidithion +1, amidothioate + I, amiton + I, amiton hydrogen oxalate + I, amitraz + I, aramite + I, arsenous oxide + I, azobenzene + I, azothoate + I, benomyl + I, benoxafos + I, benzyl benzoate + I, bixafen + I, brofenvalerate + I, bromocyclen + I, bromophos + I, bromopropylate + I, buprofezin + I, butocarboxim + I, butoxycarboxim + I, butylpyridaben + I, calcium polysulfide + I, 30 camphechlor + I, carbanolate + I, carbophenothion + I, cymiazole + I, chinomethionat + I, chlorbenside + I, chlordimeform + I, chlordimeform hydrochloride + I, chlorfenethol + I, chlorfenson + I, chlorfensulfide + I, chlorobenzilate +1, chloromebuform + I, chloromethiuron + I, chloropropylate + I, chlorthiophos + I, cinerin I + I, cinerin II + I, cinerins + I, closantel + I, coumaphos + I, crotamiton + I, crotoxyphos + I, eufraneb + I, cyanthoate + I, DCPM + I,

DDT +1, demephion +1, demephion-0 +1, demephion-S +1, demeton-methyl +1, demeton-0 + I, demeton-O-methyl + I, demeton-S + I, demeton-S-methyl + I, demeton-S-methylsulfon + I, dichlofluanid + I, dichlorvos + I, dicliphos + I, dienochlor + I, dimefox +1, dinex + I, dinexdiclexine + I, dinocap-4 + I, dinocap-6 + I, dinocton + I, dinopenton + I, dinosulfon + I, 5 dinoterbon + I, dioxathion + I, diphenyl sulfone + I, disulfiram + I, DNOC + I, dofenapyn + I, doramectin + I, endothion + I, eprinomectin + I, ethoate-methyl + I, etrimfos + I, fenazaflor + I, fenbutatin oxide + I, fenothiocarb + I, fenpyrad + I, fenpyroximate + I, fenpyrazamine + I, fenson + I, fentrifanil + I, flubenzimine + I, flucycloxuron + I, fluenetil + I, fluorbenside + I, FMC 1137 + 1, formetanate +1, formetanate hydrochloride +1, formparanate +1, gamma-HCH 10 +1, glyodin + I, halfenprox + I, hexadecyl cyclopropanecarboxylate + I, isocarbophos + I, jasmolin I + I, jasmolin II + I, jodfenphos + I, lindane + I, malonoben + I, mecarbam + I, mephosfolan +1, mesulfen +1, methacrifos +1, methyl bromide +1, metolcarb +1, mexacarbate + I, milbemycin oxime + I, mipafox + I, monocrotophos + I, morphothion + I, moxidectin + I, naled + I, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-315 one + I, nifluridide + I, nikkomycins + I, nitrilacarb + I, nitrilacarb 1:1 zinc chloride complex + I, omethoate + I, oxydeprofos + I, oxydisulfoton + I, pp'-DDT + I, parathion + I, permethrin + I, phenkapton + I, phosalone + I, phosfolan + I, phosphamidon + I, polychloroterpenes + I, polynactins + I, proclonol + I, promacyl + I, propoxur + I, prothidathion + I, prothoate + I, pyrethrin I + I, pyrethrin II + I, pyrethrins + I, pyridaphenthion + I, pyrimitate + I, quinalphos 20 +1, quintiofos +1, R-1492 +1, phosglycin +1, rotenone +1, schradan +1, sebufos +1, selamectin +1, sophamide +1, SSI-121 +1, sulfiram +1, sulfluramid +1, sulfotep +1, sulfur +1, diflovidazin + I, tau-fluvalinate + I, TEPP + I, terbam + I, tetradifon + I, tetrasul + I, thiafenox + I, thiocarboxime +1, thiofanox + I, thiometon + I, thioquinox +1, thuringiensin +1, triamiphos + I, triarathene + I, triazophos + I, triazuron + I, trifenofos + I, trinactin + I, vamidothion + I, 25 vaniliprole + I, bethoxazin + I, copper dioctanoate + I, copper sulfate + I, cybutryne + I, dichlone + I, dichlorophen + I, endothal + I, fentin + I, hydrated lime + I, nabam + I, quinoclamine +1, quinonamid +1, simazine + I, triphenyltin acetate +1, triphenyltin hydroxide +1, crufomate +1, piperazine +1, thiophanate + I, chloralose +1, fenthion +1, pyridin-4-amine + I, strychnine + I, 1-hydroxy-lH-pyridine-2-thione + I, 4-(quinoxalin-230 ylamino)benzenesulfonamide + I, 8-hydroxyquinoline sulfate + I, bronopol + I, copper hydroxide + I, cresol + I, dipyrithione + I, dodicin + I, fenaminosulf + I, formaldéhyde + I, hydrargaphen + I, kasugamycin + I, kasugamycin hydrochloride hydrate + I, nickel bis(dimethyldithiocarbamate) + I, nitrapyrin + I, octhilinone + I, oxolinic acid + I, oxytetracycline +1, potassium hydroxyquinoline sulfate +1, probenazole +1, streptomycin +1, streptomycin sesquisulfate + I, tecloftalam + I, thiomersal + I, Adoxophyes orana GV + I, Agrobacterium radiobacter + I, Amblyseius spp. + I, Anagrapha falcifera NPV + I, Anagrus atomus + I, Aphelinus abdominalis + I, Aphidius colemani + I, Aphidoletes aphidimyza + I, Autographa califomica NPV + I, Bacillus sphaericus Neide + I, Beauveria brongniartii + I, Chrysoperla camea + I, Cryptolaemus montrouzieri + I, Cydia pomonella GV + I, Dacnusa sibirica + I, Diglyphus isaea + I, Encarsia formosa + I, Eretmocerus eremicus + I, Heterorhabditis bacteriophora and H. megidis + I, Hippodamia convergens + I, Leptomastix dactylopii +1, Macrolophus caliginosus +1, Mamestra brassicae NPV +1, Metaphycus helvolus + I, Metarhizium anisopliae var. acridum + I, Metarhizium anisopliae var. anisopliae + I, Neodiprion sertifer NPV and N. lecontei NPV + I, Orius spp. +1, Paecilomyces fumosoroseus + I, Phytoseiulus persimilis + I, Steinernema bibionis + I, Steinemema carpocapsae + I, Steinemema feltiae + I, Steinemema glaseri + I, Steinemema riobrave + I, Steinemema riobravis + I, Steinemema scapterisci + I, Steinemema spp. + I, Trichogramma spp. + I, Typhlodromus occidentalis + I, Verticillium lecanii +1, apholate + I, bisazir + I, busulfan + I, dimatif + I, hemel + I, hempa + I, metepa + I, methiotepa + I, methyl apholate + I, morzid +1, penfluron + I, tepa + I, thiohempa + I, thiotepa + I, tretamine + I, uredepa + I, (E)-dec-5-en-lyl acetate with (E)-dec-5-en-l-ol + I, (E)-tridec-4-en-l-yl acetate + I, (E)-6-methylhept-2-en4-ol + I, (E,Z)-tetradeca-4,10-dien-l-yl acetate + I, (Z)-dodec-7-en-l-yl acetate + I, (Z)hexadec-11-enal +1, (Z)-hexadec-l l-en-l-yl acetate +1, (Z)-hexadec-13-en-l 1-yn-l-yl acetate + I, (Z)-icos-13-en-10-one + I, (Z)-tetradec-7-en-l-al + I, (Z)-tetradec-9-en-l-ol + I, (Z)tetradec-9-en-l-yl acetate + I, (7E,9Z)-dodeca-7,9-dien-l-yl acetate + I, (9Z,1 lE)-tetradeca9,11-dien-l-yl acetate + I, (9Z,12E)-tetradeca-9,12-dien-l-yl acetate + I, 14-methyloctadec-lene +1, 4-methyInonan-5-ol with 4-methylnonan-5-one +1, alpha-multistriatin +1, brevicomin +1, codlelure +1, codlemone +1, cuelure +1, disparlure +1, dodec-8-en-l-yl acetate +1, dodec9-en-l-yl acetate + I, dodeca-8 + I, 10-dien-l-yl acetate + I, dominicalure + I, ethyl 4methyloctanoate + I, eugenol + I, frontalin + I, grandlure + I, grandlure I + I, grandlure II + I, grandlure III +1, grandlure IV +1, hexalure +1, ipsdienol +1, ipsenol +1, japonilure +1, lineatin + I, litlure + I, looplure + I, medlure + I, megatomoic acid + I, methyl eugenol + I, muscalure + I, octadeca-2,13-dien-l-yl acetate + I, octadeca-3,13-dien-l-yl acetate + I, orfralure + I, oryctalure + I, ostramone + I, siglure + I, sordidin + I, sulcatol +1, tetradec-1 l-en-l-yl acetate + I, trimedlure + I, trimedlure A + I, trimedlure Bi + I, trimedlure B2 + I, trimedlure C + I, trunc-call + I, 2-(octylthio)ethanol + I, butopyronoxyl + I, butoxy(polypropylene glycol) + I, dibutyl adipate + I, dibutyl phthalate + I, dibutyl succinate + I, diethyltoluamide + I, dimethyl carbate + I, dimethyl phthalate + I, ethyl hexanediol +.1, hexamide + I, methoquin-butyl + I, methylneodecanamide + I, oxamate + I, picaridin + I, 1-dichloro-l-nitroethane + I, 1,1dichloro-2,2-bis(4-ethylphenyl)ethane + ï, 1,2-dichloropropane with 1,3-dichloropropene + I, l-bromo-2-chloroethane + I, 2,2,2-trichloro-l-(3,4-dichlorophenyl)ethyl acetate + I, 2,2dichlorovinyl 2-ethylsulfinylethyl methyl phosphate + I, 2-(l,3-dithiolan-2-yl)phenyl dimethylcarbamate +1,2-(2-butoxyethoxy)ethyl thiocyanate +1,2-(4,5-dimethyl-l,3-dioxolan2-yl)phenyl methylcarbamate + I, 2-(4-chloro-3,5-xylyloxy)ethanol + I, 2-chlorovinyl diethyl phosphate + I, 2-imidazolidone + I, 2-isovalerylindan-l,3-dione + I, 2-methyl(prop-2ynyl)aminophenyl methylcarbamate +1,2-thiocyanatoethyl laurate +1,3-bromo-l-chloroprop1-ene + I, 3-methyl-l-phenylpyrazol-5-yl dimethylcarbamate + I, 4-methyl(prop-2ynyl)amino-3,5-xylyl methylcarbamate + I, 5,5-dimethyl-3-oxocyclohex-l-enyl dimethylcarbamate + I, acethion + I, acrylonitrile + I, aldrin + I, allosamidin + I, allyxycarb + I, alpha-ecdysone + I, aluminium phosphide + I, aminocarb + I, anabasine + I, athidathion + I, azamethiphos + I, Bacillus thuringiensis delta endotoxins + I, barium hexafluorosilicate + I, barium polysulfide + I, barthrin + I, Bayer 22/190 + I, Bayer 22408 + I, beta-cyfluthrin + I, beta-cypermethrin + I, bioethanomethrin + I, biopermethrin + I, bis(2-chloroethyl) ether + I, borax + I, bromfenvinfos + I, bromo-DDT + I, bufenearb + I, butacarb + I, butathiofos + I, butonate +1, calcium arsenate +1, calcium cyanide +1, carbon disulfide +1, carbon tetrachloride + I, cartap hydrochloride + I, cevadine + I, chlorbicyclen + I, chlordane + I, chlordecone + I, chloroform + I, chloropicrin + I, chlorphoxim + I, chlorprazophos + I, cis-resmethrin + I, cismethrin + I, clocythrin + I, copper acetoarsenite + I, copper arsenate + I, copper oleate + I, coumithoate + I, cryolite + I, CS 708 + I, cyanofenphos + I, cyanophos + I, cyclethrin + I, cythioate + I, d-tetramethrin + I, DAEP + I, dazomet + I, decarbofuran + I, diamidafos + I, dicapthon + I, dichlofenthion + I, dicresyl + I, dicyclanil + I, dieldrin + I, diethyl 5methylpyrazol-3-yl phosphate + I, dilor + I, dimefluthrin + I, dimetan + I, dimethrin + I, dimethylvinphos + I, dimetilan + I, dinoprop + I, dinosam + I, dinoseb + I, diofenolan + I, dioxabenzofos + I, dithicrofos + I, DSP + I, ecdysterone + I, El 1642 + I, EMPC + I, EPBP + I, etaphos + I, ethiofencarb + I, ethyl formate + I, ethylene dibromide + I, ethylene dichloride +1, ethylene oxide +1, EXD +1, fenchlorphos +1, fenethacarb +1, fenitrothion +1, fenoxacrim + I, fenpirithrin + I, fensulfothion + I, fenthion-ethyl + I, flucofuron + I, fosmethilan + I, fospirate +1, fosthietan +1, furathiocarb + I, furethrin +1, guazatine +1, guazatine acétates +1, sodium tetrathiocarbonate + I, halfenprox + I, HCH + I, HEOD + I, heptachlor + I, heterophos + I, HHDN + I, hydrogen cyanide + I, hyquincarb + I, IPSP + I, isazofos + I, isobenzan + I, isodrin + I, isofenphos +1, isolane +1, isoprothiolane + I, isoxathion +1, juvénile hormone I + I, juvénile hormone II + I, juvénile hormone III + I, kelevan +1, kinoprene + I, lead arsenate +

I, leptophos + I, lirimfos + I, lythidathion + I, m-cumenyl methylcarbamate + I, magnésium phosphide + I, mazidox + I, mecarphon + I, menazon + I, mercurous chloride + I, mesulfenfos + I, metam + I, metam-potassium + I, metam-sodium + I, methanesulfonyl fluoride + I, methocrotophos + I, methoprene + I, methothrin + I, methoxychlor + I, methyl isothiocyanate + I, methylchloroform + I, methylene chloride + I, metoxadiazone + I, mirex + I, naftalofos + I, naphthalene +1, NC-170 +1, nicotine + I, nicotine sulfate +1, nithiazine +1, nomicotine +1, O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate +I, 0,0-diethyl O-4-methyl-2-oxo2H-chromen-7-yl phosphorothioate + I, Ο,Ο-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate + I, Ο,Ο,Ο',Ο'-tetrapropyl dithiopyrophosphate + I, oleic acid + I, paradichlorobenzene + I, parathion-methyl +1, pentachlorophenol + I, pentachlorophenyl laurate + I, PH 60-38 + I, phenkapton + I, phosnichlor + I, phosphine + I, phoxim-methyl + I, pirimetaphos + I, polychlorodicyclopentadiene isomers + I, potassium arsenite + I, potassium thiocyanate +1, precocene I +1, preçocene II +1, precocene III +1, primidophos +1, profluthrin + I, promecarb + I, prothiofos + I, pyrazophos + I, pyresmethrin + I, quassia + I, quinalphosmethyl +1, quinothion + I, rafoxanide + I, resmethrin + I, rotenone + I, kadethrin + I, ryania + I, ryanodine + I, sabadilla) + I, schradan + I, sebufos + I, SI-0009 + I, thiapronil + I, sodium arsenite + I, sodium cyanide + I, sodium fluoride + I, sodium hexafluorosilicate + I, sodium pentachlorophenoxide + I, sodium selenate + I, sodium thiocyanate + I, sulcofuron + I, sulcofuron-sodium + I, sulfuryl fluoride + I, sulprofos + I, tar oils + I, tazimcarb + I, TDE + I, tebupirimfos + I, temephos + I, terallethrin + I, tetrachloroethane + I, thicrofos +1, thiocyclam + I, thiocyclam hydrogen oxalate + I, thionazin + I, thiosultap + I, thiosultap-sodium + I, tralomethrin + I, transpermethrin + I, triazamate + I, trichlormetaphos-3 + I, trichloronat + I, trimethacarb + I, tolprocarb + I, triclopyricarb + I, triprene + I, veratridine + I, veratrine + I, XMC + I, zetamethrin + I, zinc phosphide + I, zolaprofos + I, and meperfluthrin + I, tetramethylfluthrin + I, bis(tributyltin) oxide + I, bromoacetamide + I, ferrie phosphate + I, niclosamide-olamine + I, tributyltin oxide + I, pyrimorph + I, trifenmorph + I, l,2-dibromo-3chloropropane + I, 1,3-dichloropropene + I, 3,4-dichlorotetrahydrothiophene 1,1-dioxide + I, 3-(4-chlorophenyl)-5-methylrhodanine + I, 5-methyl-6-thioxo-l,3,5-thiadiazinan-3-ylacetic acid + I, 6-isopentenylaminopurine + I, 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine + I, benclothiaz +1, cytokinins +1, DCIP + I, furfural +1, isamidofos +1, kinetin +1, Myrothecium verrucaria composition + I, tetrachlorothiophene + I, xylenols + I, zeatin + I, potassium ethylxanthate +1 ,acibenzolar +1, acibenzolar-S-methyl +1, Reynoutria sachalinensis extract + I, alpha-chlorohydrin + I, antu + I, barium carbonate + I, bisthiosemi + I, brodifacoum + I, bromadiolone + I, bromethalin + I, chlorophacinone + I, cholecalciferol + I, coumachlor + I, coumafuryl + I, coumatetralyl + I, crimidine + I, difenacoum +1, difethialone +1, diphacinone + I, ergocalciferol + I, flocoumafen + I, fluoroacetamide + I, flupropadine + I, flupropadine hydrochloride +1, norbormide + I, phosacetim +1, phosphorus + I, pindone +1, pyrinuron +1, scilliroside + I, sodium fluoroacetate + I, thallium sulfate + I, warfarin + I, 2-(25 butoxyethoxy)ethyl piperonylate + I, 5-(l,3-benzodioxol-5-yl)-3-hexyIcyclohex-2-enone + I, famesol with nerolidol + I, verbutin + I, MGK 264 + I, piperonyl butoxide + I, piprotal + I, propyl isomer + I, S421 + I, sesamex + I, sesasmolin + I, sulfoxide + I, anthraquinone + I, copper naphthenate + I, copper oxychloride + I, dicyclopentadiene + I, thiram + I, zinc naphthenate + I, ziram + I, imanin + I, ribavirin + I, mercuric oxide + I, thiophanate-methyl + 10 I, azaconazole + I, bitertanol + I, bromuconazole + I, cyproconazole + I, difenoconazole + I, diniconazole + I, epoxiconazole + I, fenbuconazole + I, fluquinconazole + I, flusilazole + I, flutriafol + I, furametpyr + I, hexaconazole + I, imazalil + I, imibenconazole + I, ipconazole + I, metconazole + I, myclobutanil + I, paclobutrazole + I, pefurazoate + I, penconazole + I, prothioconazole + I, pyrifenox + I, prochloraz + I, propiconazole + I, pyrisoxazole + I, 15 simeconazole + I, tebuconazole + I, tetraconazole + I, triadimefon + I, triadimenol + I, triflumizole + I, triticonazole + I, ancymidol + I, fenarimol + I, nuarimol + I, bupirimate + I, dimethirimol + I, ethirimol + I, dodemorph + I, fenpropidine + I, fenpropimorph + I, spiroxamine + I, tridemorph + I, cyprodinil +1, mepanipyrim +1, pyrimethanil + I, fenpiclonil + I, fludioxonil + I, benalaxyl + I, furalaxyl + I, metalaxyl -+ I, Rmetalaxyl + I, ofurace + I, 20 oxadixyl +1, carbendazim +1, debacarb +1, fuberidazole +1, thiabendazole +1, chlozolinate +

I, dichlozoline +1, myclozoline +1, procymidone +1, vinclozoline +1, boscalid + I, carboxin + I, fenfuram + I, flutolanil + I, mepronil + I, oxycarboxin + I, penthiopyrad + I, thifluzamide + I, dodine + I, iminoctadine + I, azoxystrobin + I, dimoxystrobin + I, enestroburin + I, fenaminstrobin + I, flufenoxystrobin + I, fluoxastrobin + I, kresoxim-methyl + I, 25 metominostrobin +1, trifloxystrobin +1, orysastrobin +1, picoxystrobin +1, pyraclostrobin +1, pyrametostrobin + I, pyraoxystrobin + I, ferbam + I, mancozeb + I, maneb + I, metiram + I, propineb + I, zineb + I, captafol + I, captan + I, fluoroimide + I, folpet + I, tolylfluanid + I, bordeaux mixture + I, copper oxide + I, mancopper +1, oxine-copper +1, nitrothal-isopropyl + I, edifenphos + I, iprobenphos + I, phosdiphen + I, tolclofos-methyl + I, anilazine + I, 30 benthiavalicarb + I, blasticidin-S + I, chloroneb + I, chlorothalonil + I, cyflufenamid + I, cymoxanil +1, cyclobutrifluram +1, diclocymet +1, diclomezine +1, dicloran +1, diethofencarb +1, dimethomorph +1, flumorph +1, dithianon +1, ethaboxam +1, etridiazole +1, famoxadone + I, fenamidone + I, fenoxanil + I, ferimzone + I, fluazinam + I, fluopicolide + I, flusulfamide + I, fluxapyroxad + I, fenhexamid + I, fosetyl-aluminium + I, hymexazol + I, iprovalicarb + I, cyazofamid + I, methasulfocarb + I, metrafenone + I, pencycuron + I, phthalide + I, polyoxins + I, propamocarb + I, pyribencarb + I, proquinazid + I, pyroquilon + I, pyriofenone + I, quinoxyfen + I, quintozene + I, tiadinil + I, triazoxide + I, tricyclazole + I, triforine + I, validamycin + I, valifenalate + I, zoxamide + I, mandipropamid + I, flubeneteram + I, 5 isôpyrazam + I, sedaxane + I, benzovindiflupyr + I, pydiflumetofen + I, 3-difluoromethyl-lmethyI-lH-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide + I, isoflucypram + I, isotianil + I, dipymetitrone + I, 6-ethyl-5,7-dioxopyrrolo[4,5][l,4]dithiino[l,2-c]isothiazole-3-carbonitrile + I, 2-(difluoromethyl)-N-[3-ethyll,l-dimethyl-indan-4-yl]pyridine-3-carboxamide + I, 4-(2,6-difluorophenyl)-6-methyl-510 phenyl-pyridazine-3-carbonitrile + I, (R)-3-(difluoromethyl)-.l-methyl-N-[l,l,3trimethylindan-4-yI]pyrazole-4-carboxamide +1, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine + I, 4- (2- bromo- 4- fluorophenyl) - N- (2chloro- 6- fluorophenyl) - 1, 3- dimethyl- 1H- pyrazol- 5- amine + I, fluindapyr + I, coumethoxystrobin (jiaxiangjunzhi) + I, Ivbenmixianan +1, dichlobentiazox + I, mandestrobin +1, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-l-yl)quinolone +1, 2-[2-fluoro-6-[(8fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol + I, oxathiapiprolin + I, tert-butyl N-[6[[[(1 -methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate + I, pyraziflumid +1, inpyrfluxam +1, trolprocarb +1, mefentrifluconazole +1, ipfentrifluconazole+ I, 2-(difluoromethyl)-N-[(3R)-3-ethyl-l,l-dimethyl-indan-4-yl]pyridine-3-carboxamide + I,

N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + I, N'-[4-(4,5dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine + I, [2-[3-[2[l-[2-[3,5-bis(difluoromethyl)pyrazol-l-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5dihydroisoxazol-5-yl]-3-chloro-phenyl] methanesulfonate + I, but-3-ynyl N-[6-[[(Z)-[(lmethyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate + I, methyl N25 [[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate + I, 3-chIoro-6methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + I, pyridachlometyl + I, 3(difluoromethyl)-l-methyl-N-[l,l,3-trimethylindan-4-yl]pyrazole-4-carboxamide + I, l-[2[[l-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyI]-4-methyl-tetrazol-5-one + I, l-methyl-4-[3-methyI-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-l30 yl)phenoxy]methyl]phenyl]tetrazol-5-one + I, aminopyrifen + I, ametoctradin + I, amisulbrom + I, penflufen + I, (Z,2E)-5-[l-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3dimethyl-pent-3-enamide + I, florylpicoxamid + I, fenpicoxamid + I, tebufloquin + I, ipflufenoquin + I, quinofumelin + I, isofetamid + I, N-[2-[2,4-dichloro-phenoxy]phenyl]-3(difluoromethyl)-l-methyl-pyrazole-4-carboxamide + I, N-[2-[2-chIoro-421382

(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1 -methyl-pyrazole-4-carboxamide + I, benzothiostrobin + I, phenamacril + I, 5-amino-l,3,4-thiadiazole-2-thiol zinc sait (2:1) + I, fluopyram + I, flutianil + I, fluopimomide + I, pyrapropoyne + I, picarbutrazox + I, 2(difluoromethyl)-N-(3-ethyl-l,l-dimethyl-indan-4-yl)pyridine-3-carboxamide + I, 25 (difluoromethyl) - N- ((3R) -1, 1,3- trimethylindan- 4- yl) pyridine- 3- carboxamide +1, 4-[[6[2-(2,4-difluorophenyl)-l, 1 -difluoro-2-hydroxy-3-(l ,2,4-triazol-l -yl)propyl]-3pyridyl]oxy]benzonitrile + I, metyltetraprole + I, 2- (difluoromethyl) - N- ((3R) - 1, 1, 3trimethylindan- 4- yl) pyridine- 3- carboxamide + I, a- (1, 1- dimethylethyl) - a- [4'(trifluoromethoxy) [1, Γ- biphenyl] - 4- yl] -5- pyrimidinemethanol + I, fluoxapiprolin + I, 10 enoxastrobin + I, 4-[[6-[2-(2,4-difluorophenyl)-l,l-difluoro-2-hydroxy-3-(l,2,4-triazol-lyl)propyl]-3-pyridyl]oxy] benzonitrile + I, 4-[[6-[2-(2,4-difluorophenyI)-l,l-difluoro-2hydroxy-3 -(5-sulfanyl-1,2,4-triazol-1 -yl)propyl]-3 -pyridyl]oxy] benzonitrile + I, 4-[[6-[2-(2,4difluoropheny 1)-1,1 -difluoro-2-hydroxy-3 -(5-thioxo-4H-1,2,4-triazol-1 -y l)propy 1] -3 pyridyl]oxy]benzonitrile + I, trinexapac + I, coumoxystrobin + I, zhongshengmycin + I, 15 thiodiazole copper + I, zinc thiazole + I, amectotractin + I, iprodione + I; N'-[5-bromo-2methyl-6-[(l S)-l -methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + I, N'-[5-bromo-2-methyl-6-[(lR)-l-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methylformamidine + I, N'-[5-bromo-2-methyl-6-(l-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethylN-methyl-formamidine +1, N'-[5-chloro-2-methyl-6-(l-methyl-2-propoxy-ethoxy)-3-pyridyl]20 N-ethyl-N-methyl-formamidine + I, N'-[5-bromo-2-methyl-6-(l-methyl-2-propoxy-ethoxy)-3pyridyl]-N-isopropyl-N-methyl-formamidine. + I (these compounds may be prepared from the methods described in WO2015/155075); N'-[5-bromo-2-methyI-6-(2-propoxypropoxy)-3pyridyl]-N-ethyl-N-methyl-formamidine +1 (this compound may be prepared from the methods described in IPCOM000249876D); N-isopropyl-N’-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-l25 hydroxy-l-phenyl-ethyl)phenyl]-N-methyl-formamidine+ I, N’-[4-(l-cyclopropyl-2,2,2trifluoro-l-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine + I (these compounds may be prepared from the methods described in WO2018/228896); Nethyl-N’-[5-methoxy-2-methyl-4-[2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyIformamidine + I, N-ethyl-N’-[5-methoxy-2-methyl-4-[2-trifuoromethyl)tetrahydrofuran-230 yl]phenyl]-N-methyl-formamidine + I (these compounds may be prepared from the methods described in WO2019/110427); N-[(lR)-l-benzyl-3-chloro-l-methyl-but-3-enyl]-8-fluoroquinoline-3-carboxamide + I, N-[(lS)-l-benzyl-3-chloro-l-methyl-but-3-enyl]-8-fluoroquinoline-3-carboxamide + I, N-[(lR)-l-benzyI-3,3,3-trifluoro-l-methyl-propyl]-8-fluoroquinoline-3-carboxamide + I, N-[(lS)-l-benzyl-3,3,3-trifluoro-l-methyl-propyl]-8-fluoro quinoline-3-carboxamide +1, N-[(lR)-l-benzyl-l,3-dimethyl-butyl]-7,8-difluoro-quinoline-3carboxamide +1, N-[(lS)-l-benzyl-l,3-dimethyl-butyl]-7,8-difIuoro-quinoline-3-carboxamide + I, 8-fluoro-N-[(LR)-l-[(3-fluorophenyl)methyl]-l ,3-dimethyl-butyl]quinoline-3carboxamide + I, 8-fluoro-N-[(lS)-l-[(3-fluorophenyl)methyl]-l,3-dimethyl-butyl]quinoline3-carboxamide +1, N-[(lR)-l-benzyl-l ,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + I, N-[(lS)-l-benzyl-l,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + I, N-((1R)-1benzyl-3-chloro-l-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + I, N-((1S)-1benzyl-3-chloro-l-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + I (these compounds may be prepared from the methods described in WO2017/153380);

l-(6,7-dimethylpyrazolo[l,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + I, 1(6,7-dimethylpyrazolo[l,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline + I, 4,4difluoro-3,3-dimethyl-l-(6-methylpyrazolo[l,5-a]pyridin-3-yl)isoquinoline + I, 4,4-difluoro3,3-dimethyl-l-(7-methylpyrazolo[l,5-a]pyridin-3-yl)isoquinoIine + I, l-(6-chloro-7-methylpyrazolo[l,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + I (these compounds may be prepared from the methods described in WO2017/025510); 1-(4,5dimethylbenzimidazol-l-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + I, 1-(4,5dimethylbenzimidazol-l-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline +1, 6-chloro-4,4-difluoro3,3-dimethyl-l-(4-methylbenzimidazol-l-yl)isoquinoline + I, 4,4-difluoro-l-(5-fluoro-4methyl-benzimidazol-l-yl)-3,3-dimethyl-isoquinoline + I, 3-(4,4-difluoro-3,3-dimethyl-lisoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole + I (these compounds may be prepared from the methods described in WO2016/156085); N-methoxy-N-[[4-[5(trifluoromethyl)-l,2,4-oxadiazol-3-yI]phenyl]methyl]cyclopropanecarboxamide + I, N,2dimethoxy-N-[[4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + I, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3yl]phenyl]methyl]propanamide + I, l-methoxy-3-methyl-l-[[4-[5-(trifluoromethyl)-l,2,4oxadiazol-3-yl]phenyl]methyl]urea + I, l,3-dimethoxy-l-[[4-[5-(trifluoromethyl)-l,2,4oxadiazol-3-yl]phenyl]methyl]urea + I, 3-ethyl-l-methoxy-l-[[4-[5-(trifluoromethyl)-l,2,4oxadiazol-3-yl]phenyl]methyl]urea + I, N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3yl]phenyl]methyl]propanamide +1, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3yl]phenyl]methyl]isoxazolidin-3-one + I, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-l,2,4oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + I, ethyl l-[[4-[5-(trifluoromethyl)-l,2,4oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate + I, N,N-dimethyl-l-[[4-[5(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]-l,2,4-triazol-3-amine + I. The compounds in this paragraph may be prepared from the methods described in WO 2017/055473,

WO 2017/055469, WO 2017/093348 and WO 2017/118689; 2-[6-(4-chlorophenoxy)-2(trifluoromethyl)-3-pyridyl]-l-(l,2,4-triazol-l-yl)propan-2-ol + I (this compound may be prepared from the methods described in WO 2017/029179); 2-[6-(4-bromophenoxy)-2(trifluoromethyl)-3-pyridyl]-l-(l,2,4-triazol-l-yl)propan-2-ol + I (this compound may be prepared from the methods described in WO 2017/029179); 3-[2-(l-chlorocycIopropyl)-3-(2fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile +1 (this compound may be prepared from the methods described in WO 2016/156290); 3-[2-(l-chlorocyclopropyl)-3-(3-chloro-2fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile +1 (this compound may be prepared from the methods described in WO 2016/156290); (4-phenoxyphenyl)methyl 2-amino-6methyl-pyridine-3-carboxylate +1 (this compound may be prepared from the methods described in WO 2014/006945); 2,6-Dimethyl-lH,5H-[l,4]dithiino[2,3-c:5,6-c']dipyrrolel,3,5,7(2H,6H)-tetrone +1 (this compound may be prepared from the methods described in WO 2011/138281); N-methy 1-4-[5-(trifluoromethy 1)-1,2,4-oxadiazo 1-3-y 1]benzenecarbothioamide + I; N-methyl-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide + I; (Z,2E)-5-[ 1-(2,4dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide + I (this compound may be prepared from the methods described in WO 2018/153707); N'-(2-chloro-5methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + I; N'-[2-chloro-4-(2fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine + I (this compound may be prepared from the methods described in WO 2016/202742); 2-(difluoromethyl)-N-[(3S)-3ethyl-l,l-dimethyl-indan-4-yl]pyridine-3-carboxamide + I (this compound may be prepared from the methods described in WO 2014/095675); (5-methyl-2-pyridyl)-[4-[5(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methanone + I, (3-methylisoxazol-5-yl)-[4-[5(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methanone + I (these compounds may be prepared from the methods described in WO 2017/220485); 2-oxo-N-propyl-2-[4-[5(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]acetamide + I (this compound may be prepared from the methods described in WO 2018/065414); ethyl l-[[5-[5-(trifluoromethyl)-l,2,4oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate + I (this compound may be prepared from the methods described in WO 2018/158365) ; 2,2-difluoro-N-methyl-2-[4-[5(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyI]acetamide +1, N-[(E)-methoxyiminomethyl]-4[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide + I, N-[(Z)-methoxyiminomethyl]-4-[5(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide + I, N-[N-methoxy-C-methylcarbonimidoyl]-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide + I (these compounds may be prepared from the methods described in WO 2018/202428).

The above described mixing partners are known. Where the active ingrédients are included in The Pesticide Manual [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: C. D. S. TomLin; The British Crop Protection Council], they are described therein under the entry number given in round brackets hereinabove for the particular compound; for example, the compound abamectin is described under entry number (1). Where [CCN] is added hereinabove to the particular compound, the compound in question is included in the Compendium of Pesticide Common Names, which is accessible on the internet [A. Wood; Compendium of Pesticide Common Names, Copyright © 1995-2004]; for example, the compound acetoprole is described under the internet address http://www.alanwood.net/pesticides/acetoprole.html.

Most of the active ingrédients described above are referred to hereinabove by a so-called common name, the relevant ISO common name or another common name being used in individual cases. If the désignation is not a common name, the nature of the désignation used instead is given in round brackets for the particular compound; in that case, the IUP AC name, the lUPAC/Chemical Abstracts name, a chemical name, a traditional name, a compound name or a develoment code is used or, if neither one of those désignations nor a common name is used, an alternative name is employed. “CAS Reg. No” means the Chemical Abstracts Registry Number.

The active ingrédient mixture of the compounds of formula (I) and an active ingrédient as described above are preferably in a mixing ratio of from 100:1 to 1:6000, especially from 50:1 to 1:50, more especially in a ratio offrom 20:1 to 1:20, even more especially from 10:1 to T. 10, very especially from 5:1 and 1:5, spécial preference being given to a ratio of from 2:1 to 1:2, and a ratio of from 4:1 to 2:1 being likewise preferred, above ail in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750. Those mixing ratios are by weight.

The mixtures as described above can be used in a method for controlling pests, which comprises applying a composition comprising a mixture as described above to the pests or their environment, with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.

The mixtures comprising a compound of formula (I) and one or more active ingrédients as described above can be applied, for example, in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingrédient components, such 5 as a “tank-mix”, and in a combined use of the single active ingrédients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days. The order of applying the compounds of formula (I) and the active ingredient(s) as described above, is not essential for working the présent invention.

The compositions according to the invention can also comprise further solid or liquid auxiliaries, such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, fertilizers or other active ingrédients for achieving spécifie effects, for example bactéricides, fungicides, nematocides, 15 plant activators, molluscicides or herbicides.

The compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid active ingrédient and in the presence of at least one auxiliary for example by intimately mixing and/or 20 grinding the active ingrédient with the auxiliary (auxiliaries). These processes for the préparation of the compositions and the use of the compounds of formula (I) for the préparation of these compositions are also a subject of the invention.

Another aspect of the invention is related to the use of a compound of formula (I) or of a 25 preferred individual compound as defined herein, of a composition comprising at least one compound of formula (I) or at least one preferred individual compound as above-defined, or of a fungicidal or insecticidal mixture comprising at least one compound of formula (I) or at least one preferred individual compound as above-defined, in admixture with other fungicides or insecticides as described above, for controlling or preventing infestation of plants, e.g. useful 30 plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g.

harvested food crops, or non-living materials by insects or by phytopathogenic microorganisms, preferably fungal organisms.

I 57

A further aspect of the invention is related to a method of controlling or preventing an infestation of plants, e.g., useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g., harvested food crops, or of non-living materials by insects or by phytopathogenic or spoilage microorganisms or organisme potentially harmful to man, 5 especially fungal organisme, which comprieee the application of a compound of formula (I) or of a preferred individual compound ae above-defmed ae active ingrédient to the plants, to parts of the plants or to the locus thereof, to the propagation material thereof, or to any part of the non-living materials.

Controlling or preventing means reducing infestation by phytopathogenic or spoilage microorganisms or organisme potentially harmful to man, especially fungal organisme, to euch a level that an improvement is demonstrated.

A preferred method of controlling or preventing an infestation of crop plants by 15 phytopathogenic microorganisms, especially fungal organisms, or insects which comprises the application of a compound of formula (I), or an agrochemical composition which contains at least one of said compounds, is foliar application. The frequency of application and the rate of application will dépend on the risk of infestation by the corresponding pathogen or insect. However, the compounds of formula (I) can also penetrate the plant through the roots via the 20 soi! (systemic action) by drenching the locus of the plant with a liquid formulation, or by applying the compounds in solid form to the soil, e.g. in granular form (soil application). In crops of water rice such granulates can be applied to the flooded rice field. The compounds of formula I may also be applied to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fongicide or coating them with a solid formulation.

A formulation, e.g. a composition containing the compound of formula (I), and, if desired, a solid or liquid adjuvant or monomers for encapsulating the compound of formula (I), may be prepared in a known manner, typically by intimately mixing and/or grinding the compound with extenders, for example solvents, solid carriers and, optionally, surface active compounds 30 (surfactants).

Advantageous rates of application are normally from 5g to 2kg of active ingrédient (a.i.) per hectare (ha), preferably from 10g to 1kg a.i./ha, most preferably from 20g to 600g a.i./ha. When ι

used as seed drenching agent, convenient dosages are from lOmg to 1g of active substance per kg of seeds.

When the combinations of the présent invention are used for treating seed, rates of 0.001 to 50 g of a compound of formula I per kg of seed, preferably from 0.01 to 10g per kg of seed are generally suffïcient.

Suitably, a composition comprising a compound of formula (I) according to the présent invention is applied either préventative, meaning prior to disease development or curative, 10 meaning after disease development.

The compositions of the invention may be employed in any conventional form, for example in the form of a twin pack, a powder for dry seed treatment (DS), an émulsion for seed treatment (ES), a flowable concentrate for seed treatment (FS), a solution for seed treatment (LS), a water dispersible powder for seed treatment (WS), a capsule suspension for seed treatment (CF), a gel for seed treatment (GF), an émulsion concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an émulsion, water in oil (EO), an émulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

Such compositions may be produced in conventional manner, e.g. by mixing the active ingrédients with appropriate formulation inerts (diluents, solvents, fillers and optionally other formulating ingrédients such as surfactants, biocides, anti-freeze, stickers, thickeners and compounds that provide adjuvancy effects). Also conventional slow release formulations may be employed where long lasting efficacy is intended. Particularly formulations to be applied in spraying forms, such as water dispersible concentrâtes (e.g. EC, SC, DC, OD, SE, EW, EO and the like), wettable powders and granules, may contain surfactants such as wetting and dispersing agents and other compounds that provide adjuvancy effects, e.g. the ondensation product of formaldéhyde with naphthalene sulphonate, an alkylarylsulphonate, a lignin sulphonate, a fatty alkyl sulphate, and ethoxylated alkylphenol and an ethoxylated fatty alcohol.

A seed dressing formulation is applied in a manner known per se to the seeds employing the combination of the invention and a diluent in suitable seed dressing formulation form, e.g. as an aqueous suspension or in a dry powder form having good adhérence to the seeds. Such seed dressing formulations are known in the art. Seed dressing formulations may contain the single active ingrédients or the combination of active ingrédients in encapsulated form, e.g. as slow release capsules or microcapsules.

In general, the formulations include from 0.01 to 90% by weight of active agent, from 0 to 20% agriculturally acceptable surfactant and 10 to 99.99% solid or liquid formulation inerts and adjuvant(s), the active agent consisting of at least the compound of formula (I) optionally together with other active agents, particularly microbiocides or conservatives or the like. Concentrated forms of compositions generally contain in between about 2 and 80%, preferably between about 5 and 70% by weight of active agent. Application forms of formulation may for example contain from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight of active agent. Whereas commercial products will preferably be formulated as concentrâtes, the end user will normally employ diluted formulations.

Whereas it is preferred to formulate commercial products as concentrâtes, the end user will normally use dilute formulations.

EXAMPLES

The Examples which follow serve to illustrate the invention. The compounds of the invention can be distinguished from known compounds by virtue of greater efficacy at low application rates, which can be verifïed by the person skilled in the art using the experimental procedures outlined in the Examples, using lower application rates if necessary, for example 60 ppm, 20 ppm or 2 ppm.

Compounds of formula (I) may possess any number of benefits including, inter alia, advantageous levels of biological activity for protecting plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingrédients (for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile (including improved crop tolérance), improved physico-chemical properties, or increased biodegradability).

Throughout this description, températures are given in degrees Celsius and “m.p.” means melting point. LC/MS means Liquid Chromatography Mass Spectroscopy and the description of the apparatus and the methods is as follows:

Method G:

Spectra were recorded on a Mass Spectrometer from Waters (SQD, SQDII Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive and négative ions), Capillary: 3.00 kV, Cône range: 30 V, Extràctor: 2.00 V, Source Température: 150°C,

Desolvation Température: 350°C, Cône Gas Flow: 50 l/h, Desolvation Gas Flow: 650 L/h, Mass range: 1Ô0 to 900 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment, diode-array detector and ELSD detector. Column: Waters UPLC HSS T3, 1.8 pm, 30 x 2.1 mm, Temp: 60 °C, DAD Wavelength range (nm): 210 to 500, Solvent Gradient: A = water + 5% MeOH + 0.05 % HCOOH, B= Acetonitrile + 0.05 % HCOOH, gradient: ΙΟΙ 5 100% B in 1.2 min; Flow (mL/min) 0.85

Method H:

Spectra were recorded on a Mass Spectrometer from Waters (SQD, SQDII Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive and négative ions),

Capillary: 3.00 kV, Cône range: 30V, Extràctor: 2.00 V, Source Température: 150°C, Desolvation Température: 350°C, Cône Gas Flow: 50 L/h, Desolvation Gas Flow: 650 L/h, Mass range: 100 to 900 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment, diode-array detector and ELSD detector. Column: Waters UPLC HSS T3, 1.8 pm, 30 x 2.1 mm, Temp: 60 °C, DAD Wavelength range (nm): 210 to 500, Solvent Gradient:

A = water + 5% MeOH + 0.05 % HCOOH, B= Acetonitrile + 0.05 % HCOOH, gradient: ΙΟΙ 00% B in 2.7 min; Flow (mL/min) 0.85

Where necessary, enantiomerically pure final compounds may be obtained from racemic materials as appropriate via standard physical séparation techniques, such as reverse phase chiral chromatography, or through stereoselective synthetic techniques, eg, by using chiral starting materials.

Formulation Examples

Wettable powders	a)	b)	c)
active ingrédient [compound of formula (I)]	25%	50%	75 %
sodium lignosulfonate	5%	5 %	-
sodium lauryl sulfate	3 %	-	5 %
sodium diisobutylnaphthalenesulfonate	-	6%	10%
phénol polyethylene glycol ether	-	2%	-
(7-8 mol of ethylene oxide) '
highly dispersed silicic acid	5 %	10%	10%
Kaolin	62%	27%

The active ingrédient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.

Powders for dry seed treatment	a)	b)	c)
active ingrédient [compound of formula (I)]	25%	50%	75%
light minerai oil	5%	5%	5%
highly dispersed silicic acid	5%	5%	-
Kaolin	65%	40%	-
Talcum	-		20%

The active ingrédient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.

Emulsifiable concentrate

active ingrédient [compound of formula (I)] octylphenol polyethylene glycol ether (4-5 mol of ethylene oxide) calcium dodecylbenzenesulfonate castor oil polyglycol ether (35 mol of ethylene oxide) Cyclohexanone xylene mixture

10 % 3 % 3% 4% 30% 50 %

Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.

Dusts	a)	b)	c)
Active ingrédient [compound of formula (I)]	5%	6%	4%
Talcum	95%	-	-
Kaolin	-	94%	-
minerai Aller	-	-	96%

Ready-for-use dusts are obtained by mixing the active ingrédient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.

Extruded granules

Active ingrédient [compound of formula (I)] 15 % sodium lignosulfonate 2 %

Carboxymethylcellulose 1 %

Kaolin 82 %

The active ingrédient is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

Coated granules

Active ingrédient [compound of formula (I)] 8 % polyethylene glycol (mol. wt. 200) 3 %

Kaolin 89 %

The fïnely ground active ingrédient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.

Suspension concentrate active ingrédient [compound of formula (I)] 40 % propylene glycol 10% nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 %

Sodium lignosulfonate 10%

Carboxymethylcellulose 1 % silicone oil (in the form of a 75 % émulsion in water) 1 %

Water 32 %

The fînely ground active ingrédient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

Flowable concentrate for seed treatment active ingrédient [compound of formula (I)] . 40 % propylene glycol 5 % copolymer butanol PO/EO 2 % tristyrenephenole with 10-20 moles EO 2 %

1,2-benzisothiazolin-3-one (in the form of a 20% solution in water) 0.5 % monoazo-pigment calcium sait 5 %

Silicone oil (in the form of a 75 % émulsion in water) 0.2 %

Water 45.3 %

The fînely ground active ingrédient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

Slow-Release Capsule Suspension parts of a combination of the compound of formula (I) are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is achieved. To this émulsion a mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed.

The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingrédients. The medium capsule diameter is 8-15 microns.

The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.

List of Abbreviations:

Aq. br s	= aqueous = broad singlet
°C	= degrees Celsius
DCM	= dichloromethane
dd	= doublet of doublet
DMF	= dimethylformamide
DMSO	= dimethyl sulfoxide
DMSO-Jd	= deuterated dimethyl sulfoxide
d	= doublet
EtOAc	= ethyl acetate
equiv. h	= équivalent = hour(s)
M	= molar
m	= multiplet
min	= minutes
MHz	= mega hertz
mp Pd2(dba)3	= melting point = tris(dibenzylideneacetone)dipalladium(0)

Pd(dppf)Cl₂ DCM = [l,l'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), DCM

complex Pd(PPh3)2Cl2	= bis(triphenylphosphine) palladium (II) dichloride
ppm RT	= parts per million = room température
Rt	= rétention time .
s	= singlet
t	= triplet

THF = tetrahydrofuran

LC/MS = Liquid Chromatography Mass Spectrometry (description of the apparatus and the methods used for LC/MS analysis are given above)

X-Phos Pd G2 = chloro(2-dicyclohexylphosphmo-2',4',6'-triisopropyl-l,T-biphenyl)[2-(2'amino-1,1 '-biphenyl)]palladium(II)

Préparation examples:

Example 1 : This example illustrâtes the préparation of methyl (Z)-2-[5-(cyclohexen-l-yl)-2methyl-phenoxy]-3-methoxy-prop-2-enoate (Compound F.2 of Table F below)

Step 1: Préparation of methyl 2-(5-bromo-2-methyl-phenoxy)acetate

To a solution of 5-bromo-2-methylphenol (53.47 mmol, 10.00 g) and methyl 2-bromoacetate (1.5 equiv., 80.20 mmol, 12.27 g, 7.44 mL) in tetrahydrofuran (0.5 moI/L, 106.9 mL) at room température was added potassium carbonate (2 equiv., 106.9 mmol, 14.78 g), and the light brown suspension was heated to 65 °C for 2 h and then allowed to cool down to room température ovemight. The reaction mixture was diluted with EtOAc and washed with water. The aqueous phase was extracted with EtOAc, and the total combined organic layer was washed with water, brine, dried with Na2SO4, filtered and concentrated in vacuo to give methyl 2-(5bromo-2-methyl-phenoxy)acetate (47.22 mmol, 15.89 g, 88% yield) as a brown liquid. The crude oil was slightly contaminated with residual methyl-2-bromoacetate, but was taken directly to the next step without further purification.

LCMS (Method H), Rt = 1.59 min, MS: (M+l) = 259,261; HNMR (400 MHz, CDC1₃) δ ppm 2.25 (s, 3 H) 3.84 (s, 3 H) 4.66 (s, 2 H) 6.84 (d, 1 H) 7.05 (m, 2 H)

Step 2: Préparation of methyl (Z)-2-(5-bromo-2-methyl-phenoxv~)-3-methoxy-prop-2-enoate

Part 1 : To a solution of 2-(5-bromo-2-methyl-phenoxy)acetate (20.8 g, 80.3 mmol) and methyl formate (6.0 equiv., 482 mmol, 29.5 g, 30.5 mL) in tetrahydrofuran (0.5 mol/L, 161 mL) at room température under argon was added sodium methoxide (20 equiv., 161 mmol, 9.13 g) portionwise. The reaction was slightly exothermic and was kept below 30 °C with the assistance of a room température water bath. The reaction mixture was stirred at room température for 1 h and quenched by the slow addition of ah aqueous saturated solution of NaHCCh. The two phases were separated and the aqueous phase was extracted with EtOAc. The total combined organic layer was washed with aqueous saturated solution of NaHCCh, brine, dried with NazSCL, filtered and concentrated in vacuo to give methyl-2-(5-bromo-2-methyl-phenoxy)-3hydroxy-prop-2-enoate, which was taken directly to the next step without further purification. LCMS (Method G), Rt = 0.80 and 0.90 min, MS: (M+l) = 287, 289

Part 2: To a solution of the crude methyl-2-(5-bromo-2-methyl-phenoxy)-3-hydroxy-prop-2enoate and dimethyl sulfate (1.2 equiv., 93.2 mmol, 11.8 g, 8.8 mL) in DMF (0.5 mol/L, 155 mL) at room température under argon was added potassium carbonate (1.5 equiv., 117 mmol, 16.3 g), and the reaction mixture was stirred at room température for 2 h. The reaction mixture was quenched by the slow addition of water, and the mixture was extracted with EtOAc. The total combined organic layer was washed with aqueous saturated solution of NaHŒh, brine, dried with Na2SÛ4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (cyclohexane:EtOAc) to give methyl (Z)-2-(5-bromo-2-methyl-phenoxy)-3methoxy-prop-2-enoate (59.6 mmol, 18.0 g, 75 % yield) as an off-white solid.

LCMS (Method G), Rt = 1.02 min, MS: (M+l) = 301, 303; ^NMR (400 MHz, CDC1³) δppm 2.31 (s, 3 H) 3.74 (s, 3 H) 3.91 (s, 3 H) 6.86 (d, 1 H) 7.05 (m, 2 H) 7.35 (s, 1 H)

Step 3: Préparation of methyl (Z')-2-r5-('cvclohexen-I-yl)-2-methyl-phenoxv1-3-methoxyprop-2-enoate

To a solution of methyl (Z)-2-(5-bromo-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (203 mg, 0.67 mmol, 1.00 equiv.), in 1,4-dioxane (6 mL) and water (1 mL) was added cyclohexen1-ylboronic acid (93.4 mg, 0.74 mmol, 1.10 equiv.), potassium phosphate (295 mg, 1.35 mmol, 2.00 equiv.) and X Phos Pd G2 (53.0 mg, 0.07 mmol, 0.10 equiv.). The reaction mixture was stirred at 100°C for 15 min and the heating source was removed. After the contents reached RT, was diluted with EtOAc and a saturated aqueous NaHCCh solution then extracted with EtOAc. The total combined organic fraction was washed with and a saturated aqueous NaHCOj solution and brine, dried with Na₂SÛ4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (cyclohexane:EtOAc) to give methyl (Z)-2-[5-(cyclohexen-l-yl)-2methyl-phenoxy]-3-methoxy-prop-2-enoate as an amorphous solid.

LC-MS (Method G), R_t = 1.17 min, MS: (M+H) = 303; Ή NMR (400 MHz, CDC1₃) δ ppm 7.36 (s, 1H), 7.11 (d, 1H), 6.96 (dd, 1H), 6.77 (d, 1H), 6.04 (m, 1H), 3.90 (s, 3H), 3.74 (s, 3H), 2.36 (m, 5H), 2.17 - 2.25 (m, 2H), 1.74 - 1.83 (m, 2H), 1.63 - 1.71 (m, 2H).

Example 2: This example illustrâtes the préparation of methyl (Z)-2-(5-cycIohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoate (Compound E.15 of Table E below)

To a solution of methyl (Z)-2-[5-(cyclohexen-l-yl)-2-methyl-phenoxy]-3-methoxy-prop-2enoate (132 mg, 0.44 mmol, 1.00 equiv.), in hexane (0.87 mL) and EtOAc (2.18 mL) was added palladium on carbon (23.2 mg, 0.01 mmol, 0.02 equiv.). The reaction mixture was stirred under hydrogen atmosphère for 2 days. The reaction mixture was filtered over celite and concentrated in vacuo. The résultant crude residue was purified by flash chromatography (cyclohexane:EtOAc) to give methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxyprop-2-enoate as a white solid (mp: 131 - 132°C).

LC-MS (Method G), R_t = 1.21 min, MS: (M+H) = 305; Ή NMR (400 MHz, CDCI3) δ ppm ppm 7.35 (s, 1H), 7.10 (d, 1H), 6.79 (dd, 1H), 6.58 (d, 1H), 3.90 (s, 3H), 3.74 (s, 3H), 2.38

2.47 (m, 1H), 2.34 (s, 3H), 1.80-1.89 (m, 4H), 1.75 (br, 1H), 1.33 - 1.42 (m, 4H), 1.22 - 1.32 (m, 1H).

Example 3: This example illustrâtes the préparation of methyl (Z)-2-[5-(2cyclopropylcyclopropyl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate (Compound E.7 of Table E below)

To a solution of 5-bromo-2-methyl-phenol (1.00 g, 5.35 mmol, 1.00 equiv.) in DME (26.7 mL), was added an aqueous 3M Na2COa solution (5.35 mL, 16.0 mmol, 3 equiv.), 2-(2cyclopropylvinyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (1.33 mL, 6.42 mmol, 1.20 equiv.). The reaction mixture was degassed with argon, then Pd(dppf)ChCH2C12 (450 mg, 0.54 mmol, 0.10 equiv.) was introduced. The black mixture was stirred at 80°C for 2 hours, the heating source was removed, and the contents allowed to corne back at RT, diluted with EtOAc and washed with a saturated aqueous NaHCCL solution and brine. The total combined organic fraction was dried with Na2SÛ4, filtered and concentrated in vacuo. The résultant crude residue was purified by flash chromatography (cyclohexane:EtOAc) to give 5-[(E)-2cyclopropyIvinyl]-2-methyl-phenol as a reddish technical solution (50% purity).

LC-MS (Method G), R_t = 1.00 min, MS: (M+H) = 175; ‘H NMR (400 MHz, CDC1₃) δ ppm: 7.04 (d, 1H), 6.82 (dd, 1H), 6.75 (d, 1H), 6.40 (d, 1H), 5.68 (dd, 1H), 4.71 (s, 1H), 2.24 (s, 3H), 1.51-1.63 (m, 1H), 0.79 - 0.87 (m, 2H), 0.48 - 0.54 (m, 2H).

Step 2: Préparation of methyl 2-r5-r(E)-2-cyclopropylvinvl1-2-methvl-phenoxy1acetate

To a technical solution of 5-[(E)-2-cyclopropylvinyl]-2-methyl-phenol (purity: 50%, 2.70 g, 7.75 mmol, 1.00 equiv.), in DMF (15.5 mL) was added K2CO3 (3.22 g, 23.2 mmol, 3.00 equiv.) and methyl bromoacetate (2.44 g, 15.5 mmol, 2.00 equiv.). The orange solution was stirred at RT for 2 h, diluted with water and extracted with EtOAc. The total combined organic fraction was washed with water and brine, dried with Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (cyclohexane:EtOAc) to give methyl 2-[5-[(E)2-cyclopropylvinyl]-2-methyl-phenoxy]acetate as a brown oil.

LC-MS (Method G), Rt = 1.12 min, MS: (M+H) = 247; Ή NMR (400 MHz, CDCI3) δ ppm: 7.08 (d, 1H), 6.88 (dd, 1H), 6.66 (d, 1H), 6.42 (d, 1H), 5.67 (dd, 1H), 4.67 (s, 2H), 3.83 (s, 3H), 2.28 (s, 3H), 1.59 (s, 1H), 0.80 - 0.86 (m, 2H), 0.49 - 0.54 (m, 2H).

Step 3: Préparation of methyl 2-r5-(2-cvclopropylcyclopropyl)-2-methyl-phenoxylacetate

To a solution of diethylzinc (1 M, 5.30 mL, 5.28 mmol, 4.00 equiv.) cooled to 0°C was added a solution of trifluoroacetic acid (0.41 mL, 5.28 mmol, 4.00 equiv.) in DCM (6.60 mL). The reaction mixture was stirred at 0°C for 30 min then a solution of diiodomethane (0.43 mL, 5.28 mmol, 4.00 equiv.) in DCM (2.00 mL) was introduced and the reaction stirred for 30 min at 0°C. Next a solution of methyl 2-[5-[(E)-2-cyclopropylvinyl]-2-methyl-phenoxy]acetate (500 mg, 1.32 mmol, 1.00 equiv.) in DCM (2.00 mL) was introduced. The reaction solution was stirred for lh at 0°C then 3h at RT. After, the contents were diluted with a saturated aqueous NH4CI solution and extracted with DCM. The total combined organic fraction was washed with a saturated aqueous NaHCCh solution and brine then dried with Na2SO4, filtered, and concentrated in vacuo. The résultant crude residue was purified by flash chromatography (cyclohexane:EtOAc) to give methyl 2-[5-(2-cyclopropylcyclopropyl)-2-methylphenoxy]acetate as a colourless oil.

LC-MS (Method G), R_t = 1.17 min, MS: (M+H) = 261;^XH NMR (400 MHz, CDC1₃) δ ppm: 7.04 - 7.06 (m, 1H), 6.59 (dd, 1H), 6.44 (d, 1H), 4.65 (s, 2H), 3.83 (s, 3H), 2.25 (s, 3H), 1.601.67 (m, 1H), 1.06 - 1.16 (m, 1H), 0.91 - 0.99 (m, 1H), 0.74 (m, 2H), 0.38 - 0.48 (m, 2H), 0.11 - 0.20 (m, 2H).

Step 4: Préparation of methyl (Z)-2-r5-(2-cyclopropylcyclopropyl)-2-methyl-phenoxyl-3hydroxy-prop-2-enoate ,

O

To a solution of NaH (60% in oil, 155 mg, 3.87 mmol, 4.00 equiv.) in DMF (2.00 mL) at RT was added a solution of methyl 2-[5-(2-cyclopropylcyclopropyl)-2-methyl-phenoxy]acetate (420 mg, 0.97 mmol, 1 equiv.) and methyl formate (1.21 mL, 19.4 mmol, 20.0 equiv.) in DMF (2.80 mL). The brown reaction mixture was stirred at 35°C for 3h then diluted slowly with MeOH and water, acidified to pH 2-3, and extracted with EtOAc. The total combined organic fraction was washed with water and brine, dried with NaiSO4, filtered, and concentrated in vacuo. The résultant crude residue was purified by flash chromatography (cyclohexane:EtOAc) to give methyl (Z)-2-[5-(2-cyclopropylcyclopropyl)-2-methyl-phenoxy]-3-hydroxy-prop-2enoate as a brown oil.

LC-MS (Method G), R_t = 1.04 min, MS: (M+H) = 289.

Step 5: Préparation of methyl (Z)-2-r5-(2-cvclopropvlcvclopropvl)-2-methyl-phenoxvl-3methoxy-prop-2-enoate

Το a solution of methyl (Z)-2-[5-(2-cyclopropylcyclopropyl)-2-methyl-phenoxy]-3-hydroxyprop-2-enoate (400 mg, 0.69 mmol, 1.00 equiv.) in DMF (1.40 mL) at RT was added K2CO3 (288 mg, 2.08 mmol, 3.00 equiv.) and dimethyl sulfate (212 mg, 1.66 mmol, 2.40 equiv.). The brown solution was stirred at RT for 30 min, diluted with EtOAc, water and a saturated aqueous NaHCCh solution, and then extracted with EtOAc. The total combined organic fraction was washed with water and brine, dried with Na2SÛ4, filtered, and concentrated in vacuo. The résultant crude residue was purified by flash chromatography (cyclohexane:EtOAc) and by reverse phase chromatography (acetonitrile: water) to give methyl (Z)-2-[5-(2cyclopropylcyclopropyl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate as a white solid (mp: 54 - 56°C).

LC-MS (Method G), R_t = 1.14 min, MS: (M+H) = 303; Ή NMR (400 MHz, CDCI3) δ ppm: 7.33 (s, 1H), 7.03 (d, 1H), 6.57 (d, 1H), 6.44 (s, 1H), 3.89 (s, 3H), 3.73 (s, 3H), 2.31 (s, 3H), 1.55-1.62 (m, 1H), 1.05 - 1.13 (m, 1H), 0.90 - 0.99 (m, 1H), 0.67 - 0.73 (m, 2H), 0.34 - 0.47 (m, 2H), 0.07 - 0.20 (m, 2H).

Example 4: This example illustrâtes the préparation of methyl (Z)-2-(5-cycIopentyl-2-methylphenoxy)-3-methoxy-prop-2-enoate (Compound E.13 of Table E below)

Under an argon atmosphère, a zinc chloride IM THF solution (2.54 mmol) was added to a cyclopentyl magnésium bromide 2M THF solution (2.54 mmol) and the pale yellow suspension was stirred at RT for 10 min during time which a small exotherm was observed. After, a solution of methyl (Z)-2-(5-bromo-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (0.153 g, 0.51 mmol) in tetrahydrofuran (2.5 mL) and PdCh(dppf) (0.19 g, 0.025 mmol) were added and the pale yellow suspension was heated at 50°C for 3 hours. The reaction mixture was then allowed to reach RT, quenched with an aqueous saturated NH4CI solution, and extracted with tert-butyl methylether. The total combined organic fraction was then washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The résultant crude residue was purified by flash chromatography (cyclohexane:EtOAc gradient) to give 0.106 mg the title compound as a white solid ( mp 80 - 83°C).

LC-MS (Method G), R_t = 1.16 min, MS: (M+H) = 291; Ή NMR (400 MHz, CDC1₃) δ ppm: 7.35 (s, 1H), 7.09 (d, 1H), 6.82 (d, 1H), 6.60 (s, 1H), 3.90 (s, 3H), 3.72 (s, 3H), 2.91 (m, 1H), 2.32 (s, 3H), 2.10-1.97 (m, 2H), 1.85 - 1.75 (m, 2H), 1.74 - 1.65 (m, 2H), 1.60 - 1.45 (m, 2H).

Table E:

data and/or rétention times for

formula (I):
Entr y	Compound name	Structure	Rt (min)	Mass charge	Method	MP (°C)
	methyl (Z)-3- methoxy-2-[2-	F
E.l	methyl-5-[4-	I 'Χβ'τ*****				74-
	(trifluoromethyl)cycl ohexyl]phenoxy]prop	o X°Xj				78
	-2-enoate
	methyl (Z)-2-[5-(4,4dimethylcyclohexyl)-
E.2	2-methyl-phenoxy]- 3-methoxy-prop-2-	ό JL Q. JL 1 J	1.31	333	G
	enoate

to

Entr y	Compound name	Structure	Rt (min)	Mass charge	Method	MP (°C)
E.3	methyl (2)-2-(5cycloheptyl-2methy l-phenoxy)-3 methoxy-prop-2enoate		1.26	319	G
E.4 F s	methyl (Z)-3methoxy-2- [5 - [(2E)2-methoxyimino-5,5dimethylcyclohexyl]-2rnethyl3henoxy]prop-2enoate	i \ P \ O _/vIX	1.21	376	G G	—
methyl (Z)-2-[5-(5,5dimethyl-2-oxocyclohexyl)-2-		1.10	347
methvl-nhenoxvl-j- <
	III
'methoxv-oron-2- ;
enoate j
E.6 E.7	methyl (Z)-2-[5-(4,4- J> difluorocyclohexyl)- ; 1 I ' 1 ΊΓ 2-methyl-phenoxy]- î I. 3-methoxy-prop-2- ! JH Il J enoate ; θ 1				117 - 119
methyl (Z)-2-[5-(2cyclopropylcycloprop yI)-2-methylphenoxy]-3methoxy-prop-2enoate ________	XJv				54- 56

Entr y	Compound name	Structure	Rt (min)	Mass charge	Method	MP (°C)
E.8	methyl (2)-2-(2bromo-5-cyclohexylphenoxy)-3methoxy-prop-2enoate		1.20	369,371	G
E.9	methyl (2)-2-(2chloro-5-cyclohexylphenoxy)-3methoxy-prop-2enoate	CX / o y—v \	1.19	325, 327	G
E.10 E.ll	methyl (2)-2-(5cyclohexyl-2- . methoxy-phenoxy)3-methoxy-prop-2enoate methyl (2)-2-(5cyclohexyl-2-fluorophenoxy)-3methoxy-prop-2- enoate	1 /—\ ! /—\ \ / * \ / । z XJ i / W /1 / .....L	1.12 1.17	321 309	G G	—
E.12 ___ E.13	methyl (2)-2-(5cyclobutyl-2-methylphenoxy)-3methoxy-prop-2enoate _________________,__________ methyl (2)-2-(5- cyclopentyl-2methyl-phenoxy)-3 methoxy-prop-2enoate ................	i 1 o< CH Ο 1 ο 1............../.	1.13	277	G	80- 83

Entr y	Compound name	Structure	Rt (min)	Mass charge	Method	MP (°C)
E.14	methyl (2)-2-(5cyclopropyl-2methyl-phenoxy)-3methoxy-prop-2enoate	°Xjj	1.04	263	G
E.15	methyl (2)-2-(5cyclohexyl-2-methylphenoxy)-3methoxy-prop-2enoate					131- 132
E.16 ÊTF ÊTïF E.Ï9	methyl (Z)-2-(5cyclohexyl-4-fluoro2-methyl-phenoxy)3 -methoxy-prop-2enoate methyl (Z)-2-[5-(4isopropylcyclohexyl) -2-methyl-phenoxy]3 -methoxy-prop-2enoate		1.66	323	H
XQ I	1.35	347 330 335	G G G
methyl (Z)-2-[5-(4cyanocyclohexyl)-2methyl-phenoxy] -3 methoxy-prop-2enoate ________.__._________________________________________________________ methyl (Z)-3methoxy-2-[5-(4methoxycyclohexyl)2-methylphenoxy]prop-2enoate	i V < ! I Y-T? i υΖλ=ο CH !............. .......L......i........................	1.05 1.1.2

Entr y	Compound name	_ Rt Structure (min)	Mass charge	MP Method (°C)
E.20	methyl (Z)-3methoxy-2-[5-(4methoxyiminocycloh exyl)-2-methylphenoxy]prop-2enoate	V \_ Q °\ 1—* O 00	343	G
E.21	methyl (Z)-2-[5-(4ethoxyiminocyclohex yl)-2-methylphenoxy]-3methoxy-prop-2enoate	yJ’A j yJ’A 1 <) Z-Ή Tï j '----- ' LZ1 | LP	362	G
E.22 methyl (Z)-2-[5-[4-	355	j | ! i j
	'difluoromethyl)cycl ohexyl]-2-methyljhenoxy]-3methoxy-prop-2-
’enoate i
E.23 . : ;	methyl (Z)-2-[5-[4'difluoromethoxy)cyc ohexy 1] -2-methy Ijhenoxy]-3methoxy-prop-2enoate	-ü FYF .-SX Q O < L14 j	371	G ' !

Table F: Melting point (mp) data and/or rétention times (Rt) for compounds according to formula (I):

Entr y	Compound name	Structure	Rt (min)	Mass charge	Method	MP (°C)
F.l	methyl (Z)-2-[5-(3,3dimethyl-6-oxocyclohexen-1 -yl)-2methy 1-phenoxy] -3 methoxy-prop-2enoate	ί|] O				118 - 120
F.2	methyl (Z)-2-[5(cyclohexen-1 -y 1)-2 methy 1-phenoxy] -3 methoxy-prop-2enoate	Jl· JL				103 - 105
F.3 F.4 F.5	methyl (Z)-2-[5-(4,4difluorocyclohexenl-yl)-2-methyIphenoxy]-3methoxy-prop-2enoate	«jfxü				... 97
methyl (Z)-2-[5(cyclopenten-1 -y l)-2 methy 1-phenoxy] -3 methoxy-prop-2enoate	_______________	1.82	289.2	H
methyl (Z)-2-[5(cyclohepten-1 -yl)-2methy 1-phenoxy] -3 methoxy-prop-2enoate		78

Entr y	Compound name	Structure	Rt (min)	Mass charge	Method	MP (°C)
U 4 F.6	methyl (Z)-2-[5(cyclohexen-1 -yl)-4fluoro-2-methylphenoxy]-3methoxy-prop-2enoate	v v O / \ ΤΙ Λ·---\				88- 90
F.7	methyl (Z)-2-[5-[4(difluoromethyl)cycl ohexen-l-yl]-2methy 1-phenoxy] -3methoxy-prop-2enoate		1.15	353	H
F.8	methyl (Z)-2-[5-(4hydroxycyclohexenl-yl)-2-methylphenoxy]-3methoxy-prop-2enoate	Ο Cl f	0.93	319	H
F.9	methyl (Z)-2-[5-(4cyanocy clohexen-1 yl)-2-methylphenoxy]-3methoxy-prop-2enoate	J	1.06	328	H
F.10	methyl (Z)-2-[5-(4,4dimethylcyclohexenl-yl)-2-methyl}henoxy]-3methoxy-prop-2enoate		1.28	331	H

Example B: Biological examples/test methods:

Alternaria solani (early blight of tomatoes)

Tomato leaf disks are placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks are inoculated with a spore suspension of the fungus 2 days after application. The inoculated leaf disks are incubated at 23 10 °C / 21°C (day/night) and 80% rh under a light régime of 12/12 h (light/dark) in a climate cabinet and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears on untreated check disk leaf disks (5-7 days after application).

The following compounds gave at least 80% control of Alternaria solani at 200 ppm when 15 compared to untreated control under the same conditions, which showed extensive disease development:

(Compounds of Table E): E.13, E.15, E.16, E.20, E.22, E.23 (Compounds of Table F): F.l, F.7

Glomerella lagenarium syn. Colletotrichum lagenarium (anthracnose of cucurbits):

Conidia of the fungus from cryogénie storage were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The test plates were incubated at 24 °C and the inhibition of growth was determined photometrically 25 after 72 hrs at 620nm.

The following compounds gave at least 80% control of Glomerella lagenarium at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

(Compounds of Table E): E.3, E.6, E.7, E.9, E.ll, E.12, E.13, E.14, E.15, E.16, E.17, E.19, 30 E.20, E.21, E.22, E.23 (Compounds of Table F): F.l, F.2, F.3, F.4, F.5, F.6, F.7, F. 10

Erysiphe graminis f.sp. tritici (Wheat powdery mildew):

Wheat leaf segments are placed on agar in multiwell plates (24-well format) and sprayed with test solutions. After drying, the leaf disks are inoculated with spores of the fungus. After appropriate incubation the activity of a compound is assessed 7 dpi (days post inoculation) as préventive fungicidal activity.

The following compounds gave at least 80% control of Erysiphe graminis f. sp. tritici at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

(Compounds of Table E): E.l, E.2, E.3, É,5, E.6, E.7, E.8, E.9, E.10, E.ll, E.12, E.13, E.14, E.15, E.16, E.17, E.19, E.20, E.21, E.22, E.23 (Compounds of Table F): F.l, F.2, F.3, F.4, F.5, F.6, F.7, F.8, F.10 '

Monosraphella nivalis syn. Microdochium nivale, Fusarium nivale (snow mould, foot rot of cereals):

Conidia of the fungus from cryogénie storage were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The 20 test plates were incubated at 24°C and the inhibition of growth was determined photometrically after 72 hrs at 620nm.

The following compounds gave at least 80% control of Monographella nivalis at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

(Compounds of Table E): E.l, E.2, E3, E.6, E.7, E.8, E.9, E.10, E.ll, E.12, E.13, E.14, E.15, E.16, E.17, E.19, E.20, E.21, E.22, E.23 (Compounds of Table F): F.3, F.4, F.5, F.6, F.7, F.8, F. 10

Mycosphaerella arachidis syn. Cercospora arachidicola (Brown leaf spot of peanut):

Conidia of the fungus from cryogénie storage were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically after approximately 5-6 days at 620nm.

• · I . 81

The following compounds gave at least 80% control of Mycosphaerella arachidis at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

(Compounds of Table E): E.l, E.2, E.3, E.6, E.7, E.8, E.9, E.10, E.ll, E.12, E.13, E.14, E.15,

E.16, E.17, E.19, E.20, E.21, E.22, E.23 (Compounds of Table F): F.3, F.4, F.5, F.6, F.7, F.8, F. 10

Phakopsora pachvrhizi (Soybean rusf):

Soybean leaf disks are placed on agar in multiwell plates (24-well format) and sprayed with test solutions. After drying, the leaf disks are inoculated with a spore suspension of the fungus.

After appropriate incubation the activity of a compound is assessed approx.12 dpi (days after inoculation) as préventive fungicidal activity.

The following compounds gave at least 70% control of Phakopsorapachyrhizi at 60 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

(Compounds of Table E): E.12, E.13, E.14, E.15, E.20, E.21 (Compounds of Table F): F.2, F.3, F.4, F.6

Phytophthora infestans (late blight of potato/tomato):

Tomato leaf disks are placed on water agar in multiwell plates (24-well format) and sprayed with test solutions. After drying, the leaf disks are inoculated with a spore suspension of the fungus. After appropriate incubation the activity of a compound is assessed 4 dpi (days after inoculation) as préventive fungicidal activity.

The following compounds gave at least 80% control of Phytophthora infestans at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

(Compounds of Table E): E.2, E.5, E.7, E.9, E.13, E.15, E.16, E.22

Plasmopara viticola (downy mildew of grapevine):

Grape vine leaf disks are placed on agar in multiwell plates (24-well format) and sprayed with test solutions. After drying, the leaf disks are inoculated with a spore suspension of the fungus. Àfter appropriate incubation the activity of a compound is assessed 7 dpi (days after inoculation) as préventive fungicidal activity.

Ί

The following compounds gave at least 80% control of Plasmopara viticola at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

(Gompounds of Table E): E.2, E.3, E.5, E.6, E.7, E.8, E.9, E.10, E.ll, E.12, E.13, E.14, E.15,

E.16, E.19, E.20, E.21, E.22, E.23 (Compounds of Table F): F.l, F.2, F.3, F.4, F.5, F.6, F.7, F.10

Puccinia recondita (Brown rusf), curative:

Wheat leaf segments are placed on agar in multiwell plates (24-well format). The leaf segments are inoculated with a spore suspension of the fungus and sprayed with test solutions 1 day after inoculation. After appropriate incubation the activity of a compound is assessed 8 dpi (days after inoculation) as curative fungicidal activity.

The following compounds gave at least 80% control of Puccinia recondita f. sp. tritici at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

(Compounds of Table E): E.7, E.12, E.13, E.15, E.16, E.19, E.20, E.21 (Compounds of Table F): F.2, F.6, F.7,

Puccinia recondita (Brown rusf), preventative:

Wheat leaf segments are placed on agar in multiwell plates (24-well format) and sprayed with test solutions. After drying, the leaf segments are inoculated with a spore suspension of the fungus. After appropriate incubation the activity of a compound is assessed 8 dpi (days after inoculation) as preventative fungicidal activity.

The following compounds gave at least 80% control of Puccinia recondita f. sp. tritici at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

(Compounds of Table E): E.l, E.2, E.3, E.5, E.6, E.7, E.8, E.9, E.10, E.12, E.13, E.14, E.15,

E. 16, E. 19, E.20, E.21, E.22, E.23 (Compounds of Table F): F.l, F.2, F.3, F.4, F.6, F.7, F.8, F.10

Pyricularia oryzae (Rice blast):

Rice leaf segments are placed on agar in multiwell plates (24-well format) and sprayed with test solutions. After drying, the leaf disks are inoculated with a spore suspension of the fungus. After appropriate incubation the activity of a compound is assessed 5 dpi (days after inoculation) as préventive fungicidal activity.

The following compounds gave at least 80% control of Pyricularia oryzae at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

(Compounds of Table E): E.3, E.6, E.7, E.12, E.13, E.15, E.16, E.20, E.21, E.23 (Compounds of Table F): F. 1

Sclerotinia sclerotiorum (Cottony rot, white mold, etc.):

Mycelial fragments of the fungus prepared from a fresh liquid culture were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was 15 added to it. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically after 72 hrs at 620nm.

The following compounds gave at least 80% control of Sclerotinia sclerotiorum at 60 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

(Compounds of Table E): E.7, E.12, E.13, E.22, E.23 (Compounds of Table F): F.5, F.7

Comparative Data:

The biological activity of compounds E.13 and E.15 of the invention are compared to the reference compounds X-l and X-2. Reference compounds X-l and X-2 are specifically disclosed on page 16 of WO 98/03464 and page 6 of EP 0 212 859 respectively.

Example C: Comparative Biological activity e&amst. Puccinia recondita (Brown rust), curative: 30

Method; Wheat leaf segments are placed on agar in multiwell plates (24-well format). The leaf segments are inoculated with a spore suspension of the fungus and sprayed with test solutions 1 day after inoculation. After appropriate incubation the activity of a compound is assessed 8 dpi (days after inoculation) as curative fungicidal activity.

The data are presented as the percentage of disease control of each compound for the biological tests and testing rates described below in table H.

Table H - Biological activity against Puccinia recondita (Brown rusf), curative:

Compound	Compound structure	Concentration (ppm)	control (%)
Compound E.15	0^	200	100
60	100
20	90
Compound E.13	ο / O °\	200	100
60	0
20	0
Reference Compound X-l (WO 98/03464)	v H /Λ	200	0
60	0
20	0
Reference Compound X-2 (EP 0 212 859)	o^	200	0
60	0
20	0

Example D: Comparative Biological activity against Phakousorapachyrhizi (Soybean rust):

Method: Soybean plants are sprayed in a spray chamber with formulated DMSO compound solutions which are diluted to the appropriate concentration with 0.1% OCHIMA (adjuvant comprising polyethoxylated sorbitol hexaoleate and tris(2-ethylhexyl) phosphate) just before 5 spraying. Leaf disks are eut from treated plants and placed on agar into 24-well plates one day after application. After, the leaf disks are inoculated with a spore suspension of the fungus. After appropriate incubation the activity of a compound is assessed approx.12 dpi (days after inoculation) as préventive fungicidal activity.

The data are presented as the percentage of disease control of each compound for the biological tests and testing rates described below in Table I.

Table I - Biological activity against Phakopsorapachyrhizi (Soybean rust):

Compound	Compound structure	Concentration (ppm)	control (%)
Compound E.15	0^	200	99
60	97
20	51
6	0
Compound E.13	V-—' 0 cy	200	98
60	46
20	4
6	0
Reference Compound X-l (WO 98/03464)	ο^	200	63
60	0
20	0
6	0

Compound	Compound structure	Concentration (ppm)	control (%)
Référencé Compound X-2 (EP 0 212 859)	0^	200	0
60	0
20	0
6	0

Example E: Comparative Biological activity against Phakopsora pachyrhizi (Soybean rust):

Method: Compounds to be tested are prepared as DMSO solutions which are diluted to the 5 appropriate concentration with 0.025% Tween20 just before spraying. Soybean leaf disks are placed on agar in multiwell plates (24-well format) and sprayed with test solutions. After drying, the leaf disks are inoculated with a spore suspension of the fungus. After appropriate incubation the activity of a compound is assessed approx.12 dpi (days after inoculation) as préventive fungicidal activity.

The data are presented as the percentage of disease control of each compound for the biological tests and testing rates described below in Table J.

Table J - Biological activity against Phakopsorapachyrhizi (Soybean rust):

Compound	Compound structure	Concentration (ppm)	control (%)
Compound E.15		200	100
60	100

Compound	Compound structure	Concentration (ppm)	control (%)
		20	100
6	95
2	70
0.6	10
Compound E.13	°\\ / y—o \_W O °\	200	100
60	100
20	100
6	60
2	10
0.6	10
Reference Compound X-l (WO 98/03464)	jTY °\	200	100
60	100
20	80
6	35
2	0
0.6	0
Reference Compound X-2 (EP 0 212 859)	/°\ί^γί·0 0.^	200	10
60	10
20	0
6	0
2	0
0.6	0

Claims (15)

1. A compound of formula (I)

wherein ’

R¹ is selected from the group consisting of hydrogen, halogen, methyl and methoxy;

R² is selected from the group consisting of hydrogen, halogen, methyl and methoxy;

R³ is selected from the group consisting of hydrogen, halogen, methyl and methoxy;

R⁴ is C3-C?cycloalkyl or Cs-Cycycloalkenyl, wherein said cycloalkyl or cycloalkenyl is optionally substituted by 1, 2 or 3 R⁵ substituents, which may be the same or different;

R⁵ is selected from the group consisting of halogen, hydroxy, cyano, Ci-C4alkyl, C2C4alkenyl, Ci-C4haloalkyl, C2-C4haloalkenyl, cyanoCi-C4alkyl, Cs-Côcycloalkyl, C3Côhalocycloalkyl, C3-C6cycloalkylCi-C4alkyl-, C3-C6cycloalkylC2-C6alkenyI-, Ci-C4alkoxy, C3-C4alkenyloxy, C3-C4alkynyloxy, Ci-C4haloalkoxy, C3-C6cycloalkylCi-C4alkoxy-, CiCsalkoxyCi-Csalkoxy-, Ci-C5alkoxyCi-C3alkyl-, (=NOR⁶), (=0), phenoxyCi-Csalkyl-, heteroaryloxyCi-Csalkyl-, phenoxy and heteroaryloxy, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur, and wherein said phenyl or heteroaryl moieties are optionally substituted by 1, 2 or 3 R⁷ substituents, which may be the same or different;

R⁶ is selected from the group consisting of Ci-Cealkyl, Cs-Cecycloalkyl, C3CôcycloalkylCi-Cialkyl-, Cs-Cealkynyl, C3-Côalkenyl and Cs-Côhaloalkenyl;

R⁷ is selected from the group consisting of fluoro, chloro, cyano, hydroxy, methyl, ethyl, methoxy, ethoxy, difluoromethyl, trifluoromethyl, difluoromethoxy and trifluoromethoxy, or an agronomically acceptable sait thereof;

or an N-oxidê thereof.

2. The compound according to claim 1, wherein R¹ is selected from the group consisting of chloro, fluoro, bromo, methyl and methoxy.

3. The compound according to claim 1 or claim 2, wherein R¹ is methyl.

4. The compound according to any one of daims 1 to 3, wherein R² is hydrogen.

5. The compound according to any one of daims 1 to 4, wherein R³ is hydrogen or fluoro.

6. The compound according to any one of daims 1 to 5, wherein R³ is hydrogen.

7. The compound according to any one of daims 1 to 6, wherein R⁴ is Cs-Cycycloalkyl optionally substituted by 1, 2 or 3 R⁵ substituents, which may be the same or different.

8. The compound according to any one of daims 1 to 7, wherein R⁴ is C3-C7cycloalkyl optionally substituted by 1 R⁵ substituent.

9. The compound according to any one of daims 1 to 8, wherein R⁴ is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

10. The compound according to any one of daims 1 to 8, wherein each R⁵ is selected from the group consisting of halogen, Ci-C4alkyl, Ci-C4haloalkyl, C3-C6cycloalkyl, (=NOR⁶) and (=0).

r

9 ⁹⁰

11. The compound according to any one of daims 1 to 8, wherein each R⁵ is selected from the group consisting of fluoro, methyl, trifluoromethyl, cyclopropyl, (=N0CH3) and (=0).

5

12. An agrochemical composition comprising a fungicidally effective amount of a compound of formula (I) according to any one of daims 1 to 11 and an agrochemicallyacceptable diluent or carrier.

13. The composition according to daim 12, further comprising at least one additional active

10 ingrédient.

14. A method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a fungicidally effective amount of a compound of formula (I) according to any of daims 1 to 11, or a composition comprising this compound as active

15 ingrédient, is applied to the plants, to parts thereof or the locus thereof.

15. Use of a compound of formula (I) according to any one of daims 1 to 11 as a fungicide.